Aspects of Peptidomimetics

Peptide and Protein Design for Biopharmaceutical Applications

Volumn , Issue , 2009, Pages 49-131

  Maes, Veronique ^a   Tourwé, Dirk ^a  

^a VRIJE UNIVERSITEIT BRUSSEL   (Belgium)

Author keywords

Cyclic peptides and cycloretroenantiomers; Helix surface mimetics; Modified GnRH and bradykinin analogues; Modified peptides; Nonpeptide mimetics design from bioactive peptide structure; Peptide backbone modifications; Peptide chemists faced with new bioactive peptide sequence; peptide mimetic as peptidomimetic; Peptidomimetics; Pseudopeptides

Indexed keywords

EID: 84890745297     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470749708.ch3     Document Type: Chapter

References (388)

1. G. R. Marshall, A hierarchical approach to peptidomimetic design, Tetrahedron, 49, 3547-3558 (1993).
2. V. J. Hruby and P. M. Balse, Conformational and topographical considerations in designing agonist peptidomimetics from peptide leads, Curr.Med.Chem., 7, 945-970 (2000).
3. C. Adessi and C. Soto, Converting a peptide into a drug: Strategies to improve stability and bioavailability, Curr.Med.Chem., 9, 963-978 (2002).
4. M. D. Fletcher and M. M. Campbell, Partially modified retro-inverso peptides: development, synthesis, and conformational behavior, Chem.Rev., 98, 763-795 (1998).
5. G. J. Moore, Designing peptide mimetics, Trends Pharmacol.Sci., 15, 124-129 (1994).
6. A. S. Ripka andD.H. Rich, Peptidomimetic design, Curr.Opin.Chem.Biol., 2, 441-452 (1998).
7. M. Chorev, The partial retro-inverso modification: A road traveled together, Biopolymers, 80, 67-84 (2005).
8. Freidinger, R., Peptides and their retro enantiomers are topologically nonidentical, personal communication.
9. L. Scheibler and M. Chorev, Synthesis of Retro-Inverso-Peptides., In Methods of Organic Chemistry (Houben-Weyl). Synthesis of Peptides and Peptidomimetics., 4th edn., 2002, 528-551.
10. H. Tamamura, M. Mizumoto, K. Hiramatsu, S. Kusano, S. Terakubo, N. Yamamoto, J. O. Trent, Z. Wang, S. C. Peiper, H. Nakashima, A. Otaka and N. Fujii, Topochemical exploration of potent compounds using retro-enantiomer libraries of cyclic pentapeptides, Org.Biomol.Chem., 2, 1255-1257 (2004).
11. Y.-C. Chen, A. Muhlrad, A. Shteyer, M. Vidson, I. Bab and M. Chorev, Bioactive pseudopeptidic analogues and cyclostereoisomers of osteogenic growth peptide C-terminal pentapeptide, OGP(10-14), J.Med.Chem., 45, 1624-1632 (2002).
12. P. M. Fischer, The design, synthesis and application of stereochemical and directional peptide isomers: A critical review, Curr.Prot.Pept.Sci., 4, 339-356 (2003).
13. M. Molteni, C. Pesenti, M. Sani, A. Volonterio and M. Zanda, Fluorinated peptidomimetics: synthesis, conformational and biological features, J.Fluorine Chem., 125, 1735-1743 (2004).
14. A. Volonterio, S. Bellosta, F. Bravin, M. C. Bellucci, L. Bruché, G. Colombo, L. Malpezzi, S. Mazzini, S. V. Meille, M. Meli, C. Ramirez de Arellano and M. Zanda, Synthesis, structure and conformation of partially-modified retro- and retro-inverso c[NHCH(CF3)]Gly peptides, Chem.Eur.J., 9, 4510-4522 (2003).
15. M. Zanda, Trifluoromethyl group: an effective xenobiotic function for peptide backbone modification, New J.Chem., 28, 1401-1411 (2004).
16. S. Sagan, P. Karoyan, O. Lequin, G. Chassaing and S. Lavielle, N- and Ca-methylation in biologically active peptides: Synthesis, structural and functional aspects, Curr.Med.Chem., 11, 2533-2554 (2004).
17. C. Gilon, M. A. Dechantsreiter, F. Burkhart, A. Friedler and H. Kessler, Synthesis of N-Alkylated Peptides., In Methods of Organic Chemistry (Houben-Weyl). Synthesis of Peptides and Peptidomimetics., 4th edn., 2002, 215-271.
18. C. Toniolo, F. Formaggio, B. Kaptein and Q. B. Broxterman, You are sitting on a gold mine!, Synlett., 9, 1295-1310 (2006).
19. M. Tanaka, Design and synthesis of chiral alpha, alpha-disubstituted amino acids and conformational study of their oligopeptides, Chem.Pharm.Bull., 55, 349-358 (2007).
20. M. G. Hinds, J. H.Welsh, D. M. Brennand, J. Fisher, M. J. Glennie, N. G. J. Richards, D. L. Turner and J. A. Robinson, Synthesis, conformational properties, and antibody recognition of peptides containing beta-turn mimetics based on alpha-alkylproline derivatives, J.Med.Chem., 34, 1777-1789 (1991).
21. F. Formaggio, Q. B. Broxterman and C. Toniolo, Synthesis of Peptides Based on Ca-Tetrasubstituted a-Amino Acids., In Methods of Organic Chemistry (Houben-Weyl). Synthesis of Peptides and Peptidomimetics, 4th edn., 2002, 292-310.
22. P.Mathur, S. Ramakumar and V. S. Chauhan, Peptide design using a,b-dehydroamino acids: from b-turns to helical hairpins, Biopolymers (Pept.Sci), 76, 150-161 (2004).
23. M. A. Broda, E. M. Ciszak, A. E. Koziol, G. Pietrzynski and B. Rzeszotarska, Conformational investigation of a,b-dehydropeptides. XVI. b-turn tendency in Ac-Pro-DXaa-NHMe:crystallographic and theoretical studies, J.Pept.Sci., 12, 538-549 (2006).
24. R.M. Joshi and V. S. Chauhan, Synthesis of Peptides Based on a,b-Didehydro-a-Amino Acids., In Methods of Organic Chemistry (Houben-Weyl). Synthesis of Peptides and Peptidomimetics, 4th edn., 2002, 636-662.
25. V. J. Hruby, G. Li, C. Haskell-Luevano and M. Shenderovich, Design of peptides, proteins, and peptidomimetics in Chi Space, Biopolymers., 43, 219-266 (1997).
26. S. E. Gibson, N. Guillo and M. J. Tozer, Towards control of w-space: Conformationally constrained analogues of Phe, Tyr, Trp, and His, Tetrahedron, 55, 585-615 (1999).
27. S. M. Cowell, Y. S. Lee, J. P. Cain and V. J. Hruby, Exploring Ramachandran and chi space: confomationally constrained amino acids and peptides in the design of bioactive polypeptide ligands, Curr.Med.Chem., 11, 2785-2798 (2004).
28. H. Josien,O.Convert, J.-P. Berlose, S. Sagan,A. Brunissen, S. Lavielle andG.Chassaing, Topographic analysis of the S7 binding subsite of the tachykinin neurokinin-1 receptor, Biopolymers, 39, 133-147 (1996).
29. H. Josien, S. Lavielle, A. Brunissen, M. Saffroy, Y. Torrens, J.-C. Beaujouan, J. Glowinski and G. Chassaing, Design and synthesis of side-chain conformationally restricted phenylalanines and their use for structure-activity studies on tachykinin NK-1 receptor, J.Med.Chem., 37, 1601 (1994).
30. S. B. Moore, M. Grant, Y. Rew, E. Bosa, M. Fabbri, U. Kumar and M. Goodman, Synthesis and biologic activity of conformationally constrained analogues of L-363,301, J.Peptide Res., 66, 404-422 (2005).
31. C. Nemes, L. Jeannin, J. Sapi, M. Laronze, H. Seghir, F. Augé and J.-Y. Laronze, A convenient synthesis of conformationally constrained b-substituted tryptophans, Tetrahedron, 56, 5479-5492 (2000).
32. J. Affaro-Lopez,W. Yuan, B. C. Phan, J. Kamath, Q. Lou, K. S. Lam and V. J. Hruby, Discovery of a novel series of potent and selective substrate-based inhibitors of p60c-src protein tyrosine kinase: conformational and topographical constraints in peptide design, J.Med.Chem., 41, 2252-2260 (1998).
33. J. Erchegyi, B. Penke, L. Simon, S. Michaelson, S. Wenger, B. Waser, R. Cescato, J.-C. Schaer, J. C. Reubi and J. Rivier, Novel sst4-selective somatostatin (SRIF) agonists. 2. Analogueswith b-methyl-3-(2-naphtyl)alanine substitutions at position 8, J.Med.Chem., 46, 5587-5596 (2003).
34. G. Tóth, E. Ioja, C. Tömboly, S. Ballet, D. Tourwé, A. Péter, T.Martinek, N. N.Chung, P. W. Schiller, S. Benyhe and A. Borsodi, b-methyl substitution of cyclohexylalanine in Dmt-Tic-Cha-Phe peptides results in highly potent d opioid antagonists, J.Med.Chem., 50, 328-333 (2007).
35. J. Lin, S. Liao and V. J. Hruby, Syntheses of optically pure, conformationally constrained, and highly hydrophobic unusual amino acids: 2-amino-3, 3-diarylpropionic acids, J.Peptide Res., 65, 105-112 (2005).
36. M. Zhang, A. Porte, G. Diamantidis, K. Sogi, D. Kubrak, L. Resnick, S. C. Mayer, Z. Wang, A. F. Kreft and B. L. Harrison, Asymmetric synthesis of novel a-amino acids with b-branched side chains, Bioorg.Med.Chem.Lett., 17, 2401-2403 (2007).
37. J. Zhou, M. C. Ye, Z. Z. Huang and Y. Tang, Controllable enantioselective Friedel- Crafts reaction between indoles and alkylidene malonates catalyzed by pseudo-C-3-symmetric trisoxazoline copper(II) complexes, J.Org.Chem., 69, 1309-1320 (2004).
38. X. Qian, K.E. Kö ver, M. D. Shenderovich, B.-S. Lou, A. Misicka, T. Zalewska, R. Horváth, P. Davis, E. J. Bilsky, F. Porreca, H. I. Yamamura and V. J. Hruby, Newly discovered stereochemical requirements in the side-chain conformation of d opioid agonists for recognizing opioid d receptors, J.Med.Chem., 37, 1746-1757 (1994).
39. S. B. Lian, M. D. Shenderovich, Z. G. Zhang, L. Maletinska, J. Slaninova and V. J. Hruby, Substitution of the side-chain-constrained amino acids beta-methyl-20,60-dimethyl-40-methoxytyrosine in position 2 of a bicyclic oxytocin analogue provides unique insights into the bioactive topography of oxytocin antagonists, J.Am.Chem.Soc., 120, 7393-7394 (1998).
40. S. B. Liao, J. Lin, M. D. Shenderovich, Y. L. Han, K. Hasohata, P. Davis, W. Qiu, F. Porreca, H. I. Yamamura and V. J. Hruby, The stereochemical requirements of the novel delta-opioid selective dipeptide antagonist TMT-TIC, Bioorg.Med.Chem.Lett., 7, 3049-3052 (1997).
41. G. J. Roff, R. C. Lloyd and N. J. Turner, A versatile chemo-enzymatic route to enantiomerically pure beta-branched alpha-amino acids, J.Am.Chem.Soc., 126, 4098-4099 (2004).
42. W. Wang, M. Cai, C. Xiong, J. Zhang, D. Trivedi and V. J. Hruby, Design and synthesis of novel w2-constrained phenylalanine, naphtylalanine, and tryptophan analogues and their use in biologically active melantropin peptides, Tetrahedron, 58, 7365-7374 (2002).
43. D. Tourwé, E. Mannekens, T. N. T. Diem, P. Verheyden, H. Jaspers, G. Tóth, A. Péter, I. Kertész, G. Törö k, N. N. Chung and P. W. Schiller, Side chain methyl substitution in the d-opioid receptor antagonist TIPP has an important effect on the activity profile, J.Med.Chem., 41, 5167-5176 (1998).
44. J. Erchegyi, B. Waser, J.-C. Schaer, R. Cescato, J. F. Brazeau, J. Rivier and J. C. Reubi, Novel sst4-selective somatostatin (SRIF) agonists. 3. Analogues amenable to radiolabeling, J.Med.Chem., 46, 5597-5605 (2003).
45. D. M. Birney, D. C. Cole, C. E. Crosson, B. F. Kahl, B. W. Neff, T. W. Reid, K. Ren and R. D. Walkup, Use of b-methylphenylalanine (bMeF) residues to probe the nature of the interaction of substance P with its receptor: effects of bMeF-containing substance P analogues on rabbit iris smooth muscle contraction, J.Med.Chem., 38, 2478-2482 (1995).
46. J. Xu, L. Wei, R. Mathvink, J. He, Y.-J. Park, H. He, B. Leiting, K. A. Lyons, F. Marsilio, R. A. Patel, J. K. Wu, N. A. Thornberry and A. E. Weber, Discovery of potent and selective phenylalanine based dipeptidyl peptidase IV inhibitors, Bioorg.Med.Chem.Lett., 15, 2533-2536 (2005).
47. C. Cativiela and M. D. Dìaz-de-Villegas, Stereoselective synthesis of quaternary a-amino acids. Part 2: Cyclic compounds, Tetrahedron - Asymmetry, 11, 645-732 (2000).
48. P. Maity and B. Konig, Enantio- and diastereoselective syntheses of cyclic C-alphatetrasubstituted alpha-amino acids and their use to induce stable conformations in short peptides, Biopolymers, 90, 8-27 (2008).
49. M. Lasa and C. Cativiela, Synthesis of enantiomerically pure 1-amino-2-phenylcycloalkanecarboxylic acids (c(n)Phe), Synlett, 16, 2517-2533 (2006).
50. K.H. Park andM. J. Kurth, Cyclic amino acid derivatives, Tetrahedron, 58, 8629-8659 (2002).
51. U. Meyer, E. Breitling, P. Bisel and A. W. Frahm, Asymmetric Strecker synthesis of enatiopure 2,4-ethanothreonines, Tetrahedron - Asymmetry, 15, 2029-2037 (2004).
52. K. Namba, M. Kawasaki, I. Takada, S. Iwama, M. Izumida, T. Shinada and Y. Ohfune, Novel and efficient transformation of a-amino nitrile to a-imino and a-amide nitriles in asymmetric Strecker synthesis, Tetrahedron Lett., 42, 3733-3736 (2001).
53. Y. Ohfune and T. Shinada, Enantio- and diastereoselective construction of a,a-disubstituted a-amino acids for the synthesis of biologically active compounds, Eur.J.Org.Chem., 5127-5143 (2005).
54. J. Wede, F.-J. Volk and A. W. Frahm, Carbocyclic a-amino acids: asymmetric Strecker synthesis of a series of 2-alkylated 1-aminocyclopentanecarboxylic acids, Tetrahedron - Asymmetry, 11, 3231-3252 (2000).
55. A. Avenoza, J. I. Barriobero, C. Cativiela, M. A. Fernandez-Recio, J. M. Peregrina and F. Rodriguez, New synthesis of all four 1-amino-2-hydroxycyclohexanecarboxylic acids, Tetrahedron, 57, 2745-2755 (2001).
56. F.-J. Volk, M. Wagner and A. W. Frahm, Cyclobutane amino acids (CBAAs): asymmetric Strecker synthesis of enantiopure cis- and trans-2,4-methanovalines, Tetrahedron - Asymmetry, 14, 497-502 (2003).
57. M. Truong, F. Lecornué and A. Fadel, First synthesis of (1S,2S)- and (1R,2R)-1-amino-2-isopropylcyclobutanecarboxylic acids by asymmetric Strecker reaction from 2-substituted cyclobutanones, Tetrahedron - Asymmetry, 14, 1063-1072 (2003).
58. P. Bisel, E. Breitling, M. Schlauch, F.-J. Volk and A. W. Frahm, Asymmetric synthesis and chromatographic resolution of all four stereomers of the a,b-propanoleucine, Pharmazie, 56, 770-772 (2001).
59. R. P. Wurz and A. B. Charette, An expedient and practical method for the synthesis of a diverse series of cyclopropane a-amino acids and amines, J.Org.Chem., 69, 1262- 1269 (2004).
60. C. H. Stammer, Cyclopropane amino-acids (2,3-methanoamino and 3,4-methanoamino acids), Tetrahedron,46, 2231-2254 (1990).
61. M. Horikawa, Y. Shigeri, N. Yumoto, S. Yoshikawa, T. Nakajima and Y. Ohfune, Syntheses of potent Leu-enkephalin analogues possessing b-hydroxy-a,a-disubstituted-a-amino acid and their characterization to opioid receptors, Bioorg.Med.Chem.Lett., 8, 2027-2032 (1998).
62. E. Gershonov, R. Granoth, E. Tzehoval, Y. Gaoni and M. Fridkin, 1-aminocyclobutanecarboxylic acid derivatives as novel structural elements in bioactive peptides: application to tuftsin analogues, J.Med.Chem., 39, 4833-4843 (1996).
63. O.O.Grygorenko,O. S.Artamonov,G.V. Palamarchuk,R. I.Zubatyuk,O.V. Shishkin and I. V. Komarov, Stereoselective synthesis of 2,4-methanoproline homologues, Tetrahedron - Asymmetry, 17, 252-258 (2006).
64. F. Couty, G. Evano and N. Rabasso, Synthesis of enantiopure azetidine 2-carboxylic acids and their incorporation into peptides, Tetrahedron - Asymmetry, 14, 2407- 2412 (2003).
65. Z. Sajjadi and W. D. Lubell, Amino acid-azetidine chimeras: synthesis of enantiopure 3-substituted azetidine-2-carboxylic acids, J.Peptide Res., 65, 298-310 (2005).
66. I. B. Parr, S. K. Boehlein, A. B. Dribben, S. M. Schuster and N. G. J. Richards, Mapping the Aspartic Acid Binding Site of Escherichia coli Asparagine Synthetase B Using Substrate Analogues, J.Med.Chem., 39, 2367-2378 (1996).
67. A. Mamai, N. E. Hughes, A. Wurthmann and J. S. Madalengoitia, Synthesis of conformationally constrained arginine and ornithine analogues based on the 3-substituted pyrrolidine framework, J.Org.Chem., 66, 6483-6486 (2001).
68. N. Pellegrini, M. Schmitt, S. Guery and J. J. Bourguignon, New strategies towards proline derivatives as conformationally constrained arginine analogues, Tetrahedron Lett., 43, 3243-3246 (2002).
69. J. Quancard, A. Labonne, Y. Jacquot, G. Chassaing, S. Lavielle and P. Karoyan, Asymmetric synthesis of 3-substituted proline chimeras bearing polar side chains of proteinogenic amino acids, J.Org.Chem., 69, 7940-7948 (2004).
70. J. Quancard, H. Magellan, S. Lavielle, G. Chassaing and P. Karoyan, Amino-zincene-enolate cyclisation: a short access to (2S,3R)- and (2S,3S)-3-benzylprolines (3-benzylpyrrolidine-2-carboxylic acids), Tetrahedron Lett., 45, 2185-2187 (2004).
71. G. A. Flynn, A. L. Akeson, R. Dharanipragada, M. J. Genin, J. A. Malikayil, R. Pottorf, J. S. Sabol, H. Schreuder, R. Tomlinson, P. Waid, R. Barrett, J. Jacobs and S. Yanofsky, Application of conformationally restricted peptidomimetics to modeling the bound conformation of peptide antagonists with the IL-1 receptor, Lett.Pept.Sci., 5, 93-100 (1998).
72. H. I. Mosberg and H. B. Kroona, Incorporation of a novel conformationally restricted tyrosine analogue into a cyclic, d opioid receptor selective tetrapeptide (JOM-13) enhances d receptor binding affinity and selectivity, J.Med.Chem., 35, 4498-4500 (1992).
73. M. Cai, C. Cai, A. V. Mayorov, C. Xiong, C. M. Cabello, V. A. Soloshonok, J. R. Swift, D. Trivedi and V. J. Hruby, Biological and conformational study of beta-substituted prolines in MT-II template: steric effects leading to human MC5 receptor selectivity, J.Peptide Res., 63, 116-131 (2004).
74. S. Sagan, J. Quancard, O. Lequin, P. Karoyan, G. Chassaing and S. Lavielle, Conformational analysis of the C-terminal Gly-Leu-Met-NH2 tripeptide of substance P bound to the NK-1 receptor, Chem.Biol., 12, 555-565 (2005).
75. K. Sugase, M. Horikawan, M. Sugiyama and M. Ishiguro, Restriction of a peptide turn conformation and conformational analysis of guanidino group using arginineproline fused amino acids: application to mini atrial natriuretic peptide on binding to the receptor, J.Med.Chem., 47, 489-492 (2004).
76. C. Kadouri-Puchot and S. Comesse, Recent advances in asymmetric synthesis of pipecolic acid and derivatives - Review article, Amino Acids, 29, 101-130 (2005).
77. I. S. Kim, J. S. Oh, O. P. Zee and Y. H. Jung, Synthesis and conformational analysis of 3-hydroxypipecolic acid analogues via CSI-mediated stereoselective amination, Tetrahedron, 63, 2622-2633 (2007).
78. L. Le Corre and H. Dhimane, Synthesis of 5-substituted pipecolic acid derivatives as new conformationally constrained ornithine and arginine analogues, Tetrahedron Lett., 46, 7495-7497 (2005).
79. J. R. Casimir, K. Iterbeke, W. Van Den Nest, M. C. Trescol-Biemont, H. Dumortier, S. Muller, D. Gerlier, C. Rabourdin-Combe, D. Tourwé and J. Paris, Conformational restriction of the Tyr(53) side-chain in the decapeptide HEL[52-61]: effects on binding to MHC-II I-A(k) molecule and TCR recognition, J.Peptide Res., 56, 398-408 (2000).
80. P. Ruzza, L. Cesaro, D. Tourwé, A. Calderan, B. Biondi, V. Maes, I. Menegazzo, A. Osler, C. Rubini, A. Guiotto, L. A. Pinna, G. Borin and A. Donella-Deana, Spatial conformation and topography of the tyrosine aromatic ring in substrate recognition by protein tyrosine kinases, J.Med.Chem., 49, 1916-1924 (2006).
81. D. Tourwé, K. Verschueren, A. Frycia, P. Davis, F. Porreca, V. J. Hruby, G. Toth, H. Jaspers, P. Verheyden and G. VanBinst, Conformational restriction of Tyr and Phe side chains in opioid peptides: Information about preferred and bioactive side-chain topology, Biopolymers, 38, 1-12 (1996).
82. W. M. Kazmierski, H. I. Yamamura and V. J. Hruby, Topographic design of peptide neurotransmitters and hormones on stable backbone templates - relation of conformation and dynamics to bioactivity, J.Am.Chem.Soc., 113, 2275-2283 (1991).
83. P. W. Schiller, G. Weltrowska, T. M. D. Nguyen, B. C. Wilkes, N. N. Chung and C. Lemieux, TIPP[c] - A highly potent and stable pseudopeptide delta-opioid receptor antagonist with extraordinary delta-selectivity, J.Med.Chem., 36, 3182-3187 (1993).
84. P. W. Schiller, G. Weltrowska, I. Berezowska, T. M. D. Nguyen, B. C. Wilkes, C. Lemieux and N. N. Chung, The TIPP opioid peptide family: Development of delta antagonists, delta agonists, and mixed mu agonist/delta antagonists, Biopolymers, 51, 411-425 (1999).
85. D. J. Kyle, J. A. Martin, S. G. Farmer and R. M. Burch, Design and conformationalanalysis of several highly potent bradykinin receptor antagonists, J.Med.Chem., 34, 1230-1233 (1991).
86. Z. X. Ye, T. MacNeil, D. H. Weinberg, R. N. Kalyani, R. Tang, A. M. Strack, B. A. Murphy, R. T. Mosley, D. E. MacIntyre, L. H. T. Van der Ploeg, A. A. Patchett, M. J. Wyvratt and R. R. Nargund, Structure-activity relationship of linear tetrapeptides Tic-DPhe-Arg-Trp-NH2 at the human melanocortin-4 receptor and effects on feeding behaviors in rat, Peptides, 26, 2017-2025 (2005).
87. K. X. Chen, F. G. Njoroge, J. Pichardo, A. Prongay, N. Butkiewicz, N. Yao, V. Madison and V. Girijavallabhan, Potent 7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid-based macrocyclic inhibitors of hepatitis C virus NS3 protease, J.Med.Chem., 49, 567-574 (2006).
88. C. G. Wang and H. I. Mosberg, Synthesis of a novel series of topographically constrained amino-acids - benzo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids, Tetrahedron Lett., 36, 3623-3626 (1995).
89. S. Van Cauwenberghe, J. Martins, M. Gosselin, L. Hodzic, J. Butterworth and D. Tourwé, Replacement of the Tic residue by benzo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids in TIPP peptides, In: Chorev, M. and Sawyer, T. K., Peptides. Peptide Revolution: Genomics, Proteomics & Therapeutics. Proceedings of the 18th American Peptide Symposium, 665-666, 2003.
90. J. B. Thomas, R. N. Atkinson, N. A. Vinson, J. L. Catanzaro, C. L. Perretta, S. E. Fix, S. W. Mascarella, R. B. Rothman, H. Xu, C. M. Dersch, B. E. Cantrell, D. M. Zimmerman and F. I. Carroll, Identification of (3R)-7-hydroxy-N-((1S)-1-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide as a novel potent and selective opioid kappa receptor antagonist, J.Med.Chem., 46, 3127-3137 (2003).
91. S. E. Gibson, N. Guillo, J. O. Jones, I. M. Buck, S. B. Kalindjian, S. Roberts and M. J. Tozer, CCK2 receptor antagonists containing the conformationally constrained phenylalanine derivatives, including the new amino acid Xic, Eur.J.Med.Chem., 37, 379-389 (2002).
92. R. Z. Cai, S. Radulovic, J. Pinski, A. Nagy, T. W. Redding, D. B. Olsen and A. V. Schally, Pseudononapeptide bombesin antagonists containing C-terminal Trp or Tpi, Peptides, 13, 267-271 (1992).
93. Z. Darula, K. E. Kover, K. Monory, A. Borsodi, E. Mako, A. Ronai, D. Tourwé, A. Peter and G. Toth, Deltorphin II analogues with 6-hydroxy-2-aminotetralin-2-carboxylic acid in position 1, J.Med.Chem., 43, 1359-1366 (2000).
94. S. Salvadori, S. D. Bryant, C. Bianchi, G. Balboni, V. Scaranari, M. Attila and L. H. Lazarus, Phe(3)-substituted analogues of deltorphin-C - spatial conformation and topography of the aromatic ring in peptide recognition by delta-opioid receptors, J.Med.Chem., 36, 3748-3756 (1993).
95. G. Toth,Z.Darula,A. Peter, F. Fulop,D. Tourwé,H. Jaspers, P. Verheyden, Z. Bocskey, Z.Toth andA.Borsodi, Conformationally constrained deltorphin analogueswith 2-aminotetralin-2-carboxylic acid in position 3, J.Med.Chem., 40, 990-995 (1997).
96. B. S. Vig, M. Q. Zheng, T. F. Murray and J. V. Aldrich, Effects of the substitution of Phe(4) in the opioid peptide [D-Ala(8)]dynorphin A-(1-11)NH2, J.Med.Chem., 46, 4002-4008 (2003).
97. X. J. Chu, D. Bartkovitz, W. Danho, J. Swistok, A. W. H. Cheung, G. Kurylko, K. Rowan, M. Yeon, L. Franco, L. D. Qi, L. Chen and K. Yagaloff, Discovery of 1-amino-4-phenylcyclohexane-1-carboxylic acid and its influence on agonist selectivity between human melanocortin-4 and -1 receptors in linear pentapeptides, Bioorg.Med.Chem.Lett., 15, 4910-4914 (2005).
98. S. Oishi, R. G. Karki, S. U. Kang, X. Z. Wang, K. M. Worthy, L. K. Bindu, M. C. Nicklaus, R. J. Fisher and T. R. Burke, Design and synthesis of conformationally constrained Grb2 SH2 domain binding peptides employing alpha-methylphenylalanyl based phosphotyrosyl mimetics, J.Med.Chem., 48, 764-772 (2005).
99. D. Obrecht, M. Altorfer, U. Bohdal, J. Daly, W. Huber, A. Labhardt, C. Lehmann, K. Muller, R. Ruffieux, P. Schonholzer, C. Spiegler and C. Zumbrunn, Design and synthesis of novel nonpolar host peptides for the determination of the 3(10)- and alpha-helix compatibilities of alpha-amino acid building blocks: An assessment of alpha,alpha-disubstituted glycines, Biopolymers, 42, 575-626 (1997).
100. T. Satoh, M. Hirano, A. Kuroiwa and Y. Kaneko, A synthesis of optically active alpha-quaternary alpha-amino acids and esters by assembling three components, ketones, (R)-chloromethyl p-tolyl sulfoxide and sodium azide, via sulfinyloxiranes, Tetrahedron, 62, 9268-9279 (2006).
101. M. Koppitz, G. Reinhardt and A. van Lingen, Solid-phase synthesis of substituted 3-amino-30-carboxy-tetrahydrocarbazoles, Tetrahedron Lett., 46, 911-914 (2005).
102. S. Pruhs, C. Dinter, T. Blume, A. Schutz, M. Harre and H. Neh, Upscaling the solidphase synthesis of a tetrahydrocarbazole in chemical development, Org.Process Res.Dev., 10, 441-445 (2006).
103. S. J. Shuttleworth, M. E. Lizarzaburu, A. Chai and P. Coward, Identification and optimization of novel partial agonists of Neuromedin B receptor using parallel synthesis, Bioorg.Med.Chem.Lett., 14, 3037-3042 (2004).
104. R. Millet, J. F. Goossens, K. Bertrand-Caumont, P. Chavatte, R. Houssin and J. P. Henichart, Synthesis and biological evaluation of conformationally restricted derivatives of tryptophan as NK1/NK2 ligands, Lett.Pept.Sci., 6, 221-233 (1999).
105. P. W. Schiller, G. Weltrowska, T. M. D. Nguyen, B. C. Wilkes, N. N. Chung and C. Lemieux, Conformationally restricted deltorphin analogues, J.Med.Chem., 35, 3956-3961 (1992).
106. D. Tourwé, K. Iterbeke, G. Törö k, G. Laus, F. Fulop, A. Péter, F. Richard and P. Kitabgi, Pro10-Tyr11 substitutions provide potent or selective NT(8-13) analogues, In: Benedetti, E. and Pedone, C., Peptides. Proceedings of the 27th European Peptide Symposium, 304-305, Napoli, Italy, 2002.
107. G. A. Flynn, E. L. Giroux and R. C. Dage, An acyl-iminium ion cyclization route to a novel conformationally restricted dipeptide mimic - applications to angiotensinconverting enzyme-inhibition, J.Am.Chem.Soc., 109, 7914-7915 (1987).
108. S. E. Delaszlo, B. L. Bush, J. J. Doyle, W. J. Greenlee, D. G. Hangauer, T. A. Halgren, R. J. Lynch, T. W. Schorn and P. K. S. Siegl, Synthesis and use of 3-amino-4-phenyl-2-piperidones and 4-amino-2-benzazepin-3-ones as conformationally restricted phenylalanine isosteres in renin inhibitors, J.Med.Chem., 35, 833-846 (1992).
109. G. A. Flynn, D. W. Beight, S. Mehdi, J. R. Koehl, E. L. Giroux, J. F. French, P. W. Hake and R. C. Dage, Application of a conformationally restricted Phe-Leu dipeptide mimetic to the design of a combined inhibitor of angiotensin I-converting enzyme and neutral endopeptidase-24.11, J.Med.Chem., 36, 2420-2423 (1993).
110. A. M. Warshawsky, G. A. Flynn, J. R. Koehl, S. Mehdi and R. J. Vaz, The synthesis of aminobenzazepinones as anti-phenylalanine dipeptide mimics and their use in NEP inhibition, Bioorg.Med.Chem.Lett., 6, 957-962 (1996).
111. T. Le Diguarher, J. C. Ortuno, D. Shanks, N. Guilbaud, A. Pierre, E. Raimbaud, J. L. Fauchere, J. A. Hickman, G. C. Tucker and P. J. Casara, Synthesis of N,N0-disubstituted 3-aminobenzo[c] and [d]azepin-2-ones as potent and specific farnesyl transferase inhibitors, Bioorg.Med.Chem.Lett., 14, 767-771 (2004).
112. J. R. Casimir, D. Tourwé, K. Iterbeke, G. Guichard and J. P. Briand, Efficient synthesis of (S)-4-phthalimido-1,3,4,5-tetrahydro-8-(2,6-dichlorobenzyloxy)-3-oxo-2H- 2-benzazepin-2-acetic acid (Pht-Hba(2,6-Cl-2-Bn)-Gly-OH), J.Org.Chem., 65, 6487-6492 (2000).
113. K.VanRompaey, I.Van den Eynde,N.DeKimpe andD. Tourwé, A versatile synthesis of 2-substituted 4-amino-1,2,4,5-tetrahydro-2-benzazepine-3-ones, Tetrahedron, 59, 4421-4432 (2003).
114. S. Ballet, A. Frycia, J. Piron, N. N. Chung, P. W. Schiller, P. Kosson, A. W. Lipkowski and D. Tourwé, Synthesis and biological evaluation of constrained analogues of the opioid peptide H-Tyr-D-Ala-Phe-Gly-NH2 using the 4-amino-2-benzazepin-3-one scaffold, J.Peptide Res., 66, 222-230 (2005).
115. S. Ballet, A. V. Mayorov, M. Y. Cai, D. Tymecka, K. B. Chandler, E. S. Palmer, K. Van Rompaey, A. Misicka, D. Tourwé and V. J. Hruby, Novel selective human melanocortin-3 receptor ligands: Use of the 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-one (Aba) scaffold, Bioorg.Med.Chem.Lett., 17, 2492-2498 (2007).
116. S. Ballet, R. De Wachter, K. Van Rompaey, C. Tomboly, D. Feytens, G. Toth, L. Quartara, P. Cucchi, S. Meini and D. Tourwé, Bradykinin analogues containing 4-amino-2-benzazepin-3-one the scaffold at the C-terminus, J.Pept.Sci., 13, 164-170 (2007).
117. I. Van den Eynde, G. Laus, P. W. Schiller, P. Kosson, N. N. Chung, A. W. Lipkowski and D. Tourwé, A new structural motif for mu-opioid antagonists, J.Med.Chem., 48, 3644-3648 (2005).
118. S. Ballet, S. Salvadori, C. Trapella, S. D. Bryant, Y. Jinsmaa, L. H. Lazarus, L. Negri, E. Giannini, R. Lattanzi, D. Tourwé and G. Balboni, New 20,60-dimethyl-L-tyrosine (Dmt) opioid peptidomimetics based on the Aba-Gly scaffold. Development of unique mu-opioid receptor ligands, J.Med.Chem., 49, 3990-3993 (2006).
119. P. Ruzza, A. Calderan, A. Donella-Deana, B. Biondi, L. Cesaro, A. Osler, S. Elardo, A. Guiotto, L. A. Pinna and G. Borin, Conformational constraints of tyrosine in protein tyrosine kinase substrates: Information about preferred bioactive side-chain orientation, Biopolymers, 71, 478-488 (2003).
120. K. Van Rompaey, S. Ballet, C. Tomboly, R. De Wachter, K. Vanommeslaeghe, M. Biesemans, R. Willem and D. Tourwé, Synthesis and evaluation of the beta-turn properties of 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-ones and of their spirocyclic derivative, Eur.J.Org.Chem., 2899-2911 (2006).
121. K. Pulka, D. Feytens, I. Van den Eynde, R. De Wachter, P. Kosson, A. Misicka, A. Lipkowski, N. N. Chung, P. W. Schiller and D. Tourwé, Synthesis of 4-amino-3-oxo-tetrahydroazepino[3,4-b]indoles: new conformationally constrained Trp analogues, Tetrahedron, 63, 1459-1466 (2007).
122. D. Feytens, R. Cescato, J. C. Reubi and D. Tourwé, New sst(4/5)-selective somatostatin peptidomimetics based on a constrained tryptophan scaffold, J.Med.Chem., 50, 3397-3401 (2007).
123. A. F. Spatola, Peptide Backbone Modifications: a Structure-Activity Analysis of Peptides Containing Amide Bond Surrogates. Conformational Constraints, and Related Backbone Replacements., In Chemistry and Biochemistry of Amino Acids, Peptides, and Proteins, Volume 7 edn., 1983, ch. 5, 267-357.
124. S. Gupta and J. W. Payne, Evaluation of the conformational propensities of peptide isosteres as a basis for selecting bioactive pseudopeptides, J.Peptide Res., 58, 546-561 (2001).
125. P. Gillespie, J. Cicariello and G. L. Olson, Conformational analysis of dipeptide mimetics, Biopolymers., 43, 191-217 (1997).
126. D. H. Coy, S. J. Hocart and Y. Sasaki, Solid-phase reductive alkylation techniques in analogue peptide-bond and side-chain modification, Tetrahedron, 44, 835-841 (1988).
127. J. P. Meyer, P. Davis, K. B. Lee, F. Porreca, H. I. Yamamura and V. J. Hruby, Synthesis using a Fmoc-based strategy and biological-activities of some reduced peptide-bond pseudopeptide analogues of dynorphin A(1), J.Med.Chem., 38, 3462-3468 (1995).
128. N. P. Boyarskaya, D. I. Prokhorov, Y. G. Kirillova, E. N. Zvonkova and V. I. Shvets, Synthesis of protected pseudopeptides from dicarboxylic amino acids by Mitsunobu condensation, Tetrahedron Lett., 46, 7359-7362 (2005).
129. D. H. Coy, P. Heinzerian, N. Y. Jiang, Y. Sasaki, J. Taylor, J. P. Moreau, W. T. Wolfrey, J. D. Gardner and R. T. Jensen, Probing peptide backbone function in bombesin - a reduced peptide-bond analogue with potent and specific receptor antagonist activity, J.Biol.Chem., 263, 5056-5060 (1988).
130. M. Rodriguez, M. F. Lignon, M. C. Galas, P. Fulcrand, C. Mendre, A. Aumelas, J. Laur and J. Martinez, Synthesis and biological-activities of pseudopeptide analogues of the C-terminal heptapeptide of cholecystokinin - on the importance of the peptide-bonds, J.Med.Chem., 30, 1366-1373 (1987).
131. Y. Sasaki, W. A. Murphy, M. L. Heiman, V. A. Lance and D. H. Coy, Solid-phase synthesis and biological properties of c-[CH2NH] pseudopeptide analogues of a highly potent somatostatin octapeptide, J.Med.Chem., 30, 1162-1166 (1987).
132. A. Ambo, T. Adachi and Y. Sasaki, Synthesis and opioid activities of [D-Leu(8)]Dynorphin(1-8) analogues containing a reduced peptide-bond, c(CH2NH), Chem.Pharm.Bull., 43, 1547-1550 (1995).
133. J. Couder, D. Tourwé, G. VanBinst, J. Schuurkens and J. E. Leysen, Synthesis and biological-activities of c(CH2NH) pseudopeptide analogues of the C-terminal hexapeptide of neurotensin, Int.J.Pept.Protein Res., 41, 181-184 (1993).
134. D. Lugrin, F. Vecchini, S. Doulut, M.Rodriguez, J. Martinez and P. Kitabgi, Reduced peptide-bond pseudopeptide analogues of neurotensin - binding and biological-activities and in vitro metabolic stability, Eur.J.Pharmacol., 205, 191-198 (1991).
135. G. Drapeau, N. E. Rhaleb, S. Dion, D. Jukic and D. Regoli, [Phe8-c(CH2-NH)Arg9]Bradykinin, a B2-receptor selective agonist which is not broken down by either kininase-I or kininase-II, Eur.J.Pharmacol., 155, 193-195 (1988).
136. R. Bergmann, M. Scheunemann, C. Heichert, P. Mading, H. Wittrisch, M. Kretzschmar, H. Rodig, D. Tourwé, K. Iterbeke, K. Chavatte, D. Zips, J. C. Reubi and B. Johannsen, Biodistribution and catabolism of F-18-labeled neurotensin (8-13) analogues, Nucl.Med.Biol., 29, 61-72 (2002).
137. P. Blauenstein, E. G. Garayoa, D. Ruegg, A. Blanc, D. Tourwé, A. Beck-Sickinger and P. A. Schubiger, Improving the tumor uptake of Tc-99m-labeled neuropeptides using stabilized peptide analogues, Cancer Biother.Radio., 19, 181-188 (2004).
138. L. Elmasdouri, A. Aubry, C. Sakarellos, E. J. Gomez, M. T. Cung and M. Marraud, A beta-turn-like conformation in reduced peptides - crystal-structures of 2 dipeptide analogues with Pro-Gly-c[CH2NH] sequence, Int. J. Peptide Protein Res., 31, 420-428 (1988).
139. C. Toniolo, G. Valle, M. Crisma, J. S. Kaltenbronn, J. T. Repine, G. Van Binst, M. Elseviers and D. Tourwé, c[CH2NH] Backbone-modified peptides: first unequivocal observation of a C7 structure in a linear peptide, Peptide Research, 2, 332- 337 (1989).
140. A. Geyer, G. Muller and H. Kessler, Conformational-analysis of a cyclic RGD peptide-containing a c[CH2NH] bond - A positional shift in backbone structure caused by a single dipeptide mimetic, J.Am.Chem.Soc., 116, 7735-7743 (1994).
141. D. Coy, L. H. Wang, N. Y. Jiang and R. Jensen, Short chain bombesin pseudopeptides with potent bombesin receptor antagonist activity in rat and guinea-pig pancreatic acinar-cells, Eur.J.Pharmacol., 190, 31-38 (1990).
142. M. Hiramatsu, K. Inoue, A. Ambo, Y. Sasaki and T. Kameyama, Long-lasting antinociceptive effects of a novel dynorphin analogue, Tyr-D-Ala-Phe-Leu-Arg c (CH2NH) Arg-NH2, in mice, Brit.J.Pharmacol., 132, 1948-1956 (2001).
143. G. E. Feurle, H. E. Meyer and G. Hamscher, Metabolism and potency of xenin and of its reduced hexapseudopeptide c fragment in the dog, Life Sci., 74, 697-707 (2003).
144. J. Martinez, J. P. Bali, M. Rodriguez, B. Castro, R. Magous, J. Laur and M. F. Lignon, Synthesis and biological-activities of some pseudo-peptide analogues of tetragastrin - the importance of the peptide backbone, J.Med.Chem., 28, 1874-1879 (1985).
145. S. Zacharia, W. J. Rossowski, N. Y. Jiang, P. Hrbas, A. Ertan and D. H. Coy, New reduced peptide-bond substance-P agonists and antagonists - effects on smoothmuscle contraction, Eur.J.Pharmacol., 203, 353-357 (1991).
146. N. G. J. Delaet, P. M. F. Verheyden, D. Tourwé, G. VanBinst, P. Davis and T. F. Burks, Morphiceptin and beta-casomorphin-5 analogues containing a reduced peptide-bond - selective mu-receptor agonists and a novel mu antagonist, H-Tyr-Pro-c(CH2-NH) Phe-Pro-Gly-OH, Biopolymers, 32, 957-969 (1992).
147. A. Balasubramaniam, V. C. Dhawan, D. E. Mullins, W. T. Chance, S. Sheriff, M. Guzzi, M. Prabhakaran and E. M. Parker, Highly selective and potent neuropeptide Y (NPY) Y1 receptor antagonists based on [Pro(30), Tyr(32), Leu(34)]NPY (28-36)-NH2 (BW1911U90), J.Med.Chem., 44, 1479-1482 (2001).
148. G. Calo', R. Guerrini, R. Bigoni, A. Rizzi, C. Bianchi, D. Regoli and S. Salvadori, Structure-activity study of the nociceptin(1-13)-NH2 N-terminal tetrapeptide and discovery of a nociceptin receptor antagonist, J.Med.Chem., 41, 3360-3366 (1998).
149. J. R. Wisner, B. G. Xue, D. H. Coy and I. G. Renner, (D-Ala1, Leu9-c-CH2NHLeu10) Neuromedin-C antagonizes neuromedin C-stimulated amylase release by acini isolated from the rat pancreas, Pancreas, 5, 408-414 (1990).
150. Q. Y. Zhao, Q. Chen, D. J. Yang, Y. Feng, Y. Long, P. Wang and R. Wang, Endomorphin 1[c] and endomorphin 2[c], endomorphins analogues containing a reduced (CH2NH) amide bond between Tyr(1) and Pro(2), display partial agonist potency but significant antinociception, Life Sci., 77, 1155-1165 (2005).
151. M. Szelke, B. Leckie, A. Hallett, D. M. Jones, J. Sueiras, B. Atrash and A. F. Lever, Potent new inhibitors of human renin, Nature, 299, 555-557 (1982).
152. K. Suguna, E. A. Padlan, C. W. Smith, W. D. Carlson and D. R. Davies, Binding of a reduced peptide inhibitor to the aspartic proteinase from rhizopus-chinensis - implications for a mechanism of action, P.Natl.Acad.Sci.USA, 84, 7009-7013 (1987).
153. D. Skrbec and D. Romeo, Inhibition of Candida albicans secreted aspartic protease by a novel series of peptidomimetics, also active on the HIV-1 protease, Biochem.Bioph.Res.Co., 297, 1350-1353 (2002).
154. J. S. Wai, D. L. Bamberger, T. E. Fisher, S. L. Graham, R. L. Smith, J. B. Gibbs, S. D. Mosser, A. I. Oliff, D. L. Pompliano, E. Rands and N. E. Kohl, Synthesis and biological activity of Ras Farnesyl Protein Transferase inhibitors. Tetrapeptide analogues with amino methyl and carbon linkages, Bioorg.Med.Chem., 2, 939-947 (1994).
155. C. A. Coburn, S. J. Stachel, K. G. Jones, T. G. Steele, D. M. Rush, J. DiMuzio, B. L. Pietrak, M. T. Lai, Q. Huang, J. Lineberger, L. X. Jin, S. Munshi, M. K. Holloway, A. Espeseth, A. Simon, D. Hazuda, S. L. Graham and J. P. Vacca, BACE-1 inhibition by a series of c[CH2NH] reduced amide isosteres, Bioorg.Med.Chem.Lett., 16, 3635-3638 (2006).
156. T. Narumi, K. Tomita, E. Inokuchi, K. Kobayashi, S. Oishi, H. Ohno and N. Fujii, Diastereoselective synthesis of highly functionalized fluoroalkene dipeptide isosteres and its application to Fmoc-based solid-phase synthesis of a cyclic pentapeptide mimetic, Tetrahedron, 64, 4332-4346 (2008).
157. A. Niida, K. Tomita, M. Mizumoto, H. Tanigaki, T. Terada, S. Oishi, A. Otaka, K. Inui and N. Fujii, Unequivocal synthesis of (Z)-alkene and (E)-fluoroalkene dipeptide isosteres to probe structural requirements of the peptide transporter PEPT1, Org.Lett., 8, 613-616 (2006).
158. P. A. Bartlett and A. Otake, Fluoroalkenes as peptide isosteres - ground-state analogue inhibitors of thermolysin, J.Org.Chem., 60, 3107-3111 (1995).
159. P. Wipf, T. C. Henninger and S. J. Geib, Methyl- and (trifluoromethyl)alkene peptide isosteres: Synthesis and evaluation of their potential as beta-turn promoters and peptide mimetics, J.Org.Chem., 63, 6088-6089 (1998).
160. J. B. Xiao, B. Weisblum and P. Wipf, Electrostatic versus steric effects in peptidomimicry: Synthesis and secondary structure analysis of gramicidin S analogues with (E)-alkene peptide isosteres, J.Am.Chem.Soc., 127, 5742-5743 (2005).
161. E. Inokuchi, T. Narumi, A. Niida, K. Kobayashi, K. Tomita, S. Oishi, H. Ohno and N. Fujii, Efficient synthesis of trifluoromethyl and related trisubstituted alkene dipeptide isosteres by palladium-catalyzed carbonylation of amino acid derived allylic carbonates, J.Org.Chem., 73, 3942-3945 (2008).
162. R. R. Gardner, G. B. Liang and S. H. Gellman, beta-turn and beta-hairpin mimicry with tetrasubstituted alkenes, J.Am.Chem.Soc., 121, 1806-1816 (1999).
163. J. B. Xiao, B. Weisblum and P. Wipf, Trisubstituted (E)-alkene dipeptide isosteres as beta-turn promoters in the gramicidin S cyclodecapeptide scaffold, Org.Lett., 8, 4731-4734 (2006).
164. D. Tourwé, K. Iterbeke and E. Mannekens, Synthesis of Peptides Containing Carbaamide Bond Replacements, In Houben-Weyl. Methods of Organic Chemistry. Synthesis of Peptides and Peptidomimetics., 4th edn., 2003, vol. E22c, ch. 10.5, 324-372.
165. N. G. Bandur, K. Harms and U. Koert, First stereoselective synthesis of a Tyr-Tyr E-alkene isostere, Synlett., 99-102 (2007).
166. P. Wipf, J. B. Xiao and S. J. Geib, Imine additions of internal alkynes for the synthesis of trisubstituted (E)-alkene and cyclopropane peptide isosteres, Adv.Synth.Catal., 347, 1605-1613 (2005).
167. C. A. Olsen, H. Franzyk and J. W. Jaroszewski, Aziridines in parallel- and solidphase synthesis, Eur.J.Org.Chem., 1717-1724 (2007).
168. M. Wada, R. Doi, R. Hosotani, S. Higashide, T. Ibuka, H. Habashita, K. Nakai, N. Fujii and M. Imamura, Effect of a new bombesin receptor antagonist, (E)-alkene bombesin isostere, on amylase release from rat pancreatic acini, Pancreas, 10, 301-305 (1995).
169. P. Wipf and J. B. Xiao, Convergent approach to (E)-alkene and cyclopropane peptide isosteres, Org.Lett., 7, 103-106 (2005).
170. Z. Jakopin, R. Roskar and M. S. Dolenc, Synthesis of 3,5-disubstituted 1,2,4-oxadiazoles as peptidomimetic building blocks, Tetrahedron Lett., 48, 1465- 1468 (2007).
171. J. Cesar and M. Sollner, Use of 3,5-disubstituted 1,2,4-triazoles for the synthesis of peptidomimetics, Synthetic Commun., 30, 4147-4158 (2000).
172. D. D. Beusen, J. Zabrocki, U. Slomczynska, R. D. Head, J. L. F. Kao and G. R. Marshall, Conformational Mimicry - Synthesis and Solution Conformation of A Cyclic Somatostatin Hexapeptide Containing A Tetrazole Cis Amide Bond Surrogate, Biopolymers, 36, 181-200 (1995).
173. V. Brecx, P. Verheyden and D. Tourwé, Alpha-Bn-o-AMPA as a cis peptide bond mimic in somatostatin analogues, Lett.Pept.Sci., 5, 67-70 (1998).
174. A. D. Abell, Heterocyclic-based peptidomimetics, Lett.Pept.Sci., 8, 267-272 (2002).
175. J. K. Pokorski, L. M. M. Jenkins, H. Q. Feng, S. R. Durell, Y. W. Bai and D. H. Appella, Introduction of a triazole amino acid into a peptoid oligomer induces turn formation in aqueous solution, Org.Lett., 9, 2381-2383 (2007).
176. V. D. Bock, D. Speijer, H. Hiemstra and J. H. van Maarseveen, 1,2,3-triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics, Org.Biomol.Chem., 5, 971-975 (2007).
177. A. K. Ghosh, P. R. Sridhar, N. Kumaragurubaran, Y. Koh, I. T. Weber and H. Mitsuya, Bis-tetrahydrofuran: a privileged ligand for darunavir and a new generation of HIV protease inhibitors that combat drug resistance, ChemMedChem, 1, 939 ff. (2006).
178. A. Brik and C. H. Wong, HIV-1 protease: mechanism and drug discovery, Org.Biomol.Chem., 1, 5-14 (2003).
179. B. B. Scott, G. M. McGeehan and R. K. Harrison, Development of inhibitors of the aspartyl protease renin for the treatment of hypertension, Curr.Protein Pept.Sc., 7, 241-254 (2006).
180. A. K. Ghosh, G. Bilcer, C. Harwood, R. Kawahama, D. Shin, K. A. Hussain, L. Hong, J. A. Loy, C. Nguyen, G. Koelsch, J. Ermolieff and J. Tang, Structurebased design: Potent inhibitors of human brain memapsin 2 (beta-secretase), J.Med.Chem., 44, 2865-2868 (2001).
181. M. C. Maillard, R. K. Hom, T. E. Benson, J. B. Moon, S. Mamo, M. Bienkowski, A. G. Tomasselli, D. D. Woods, D. B. Prince, D. J. Paddock, T. L. Emmons, J. A. Tucker, M. S. Dappen, L. Brogley, E. D. Thorsett, N. Jewett, S. Sinha and V. John, Design, synthesis, and crystal structure of hydroxyethyl secondary aminebased peptidomimetic inhibitors of human beta-secretase, J.Med.Chem., 50, 776-781 (2007).
182. H. J. Lee, H. M. Park and K. B. Lee, The beta-turn scaffold of tripeptide containing an azaphenylalanine residue, Biophys.Chem., 125, 117-126 (2007).
183. D. Boeglin and W. D. Lubell, Aza-amino acid scanning of secondary structure suited for solid-phase peptide synthesis with Fmoc chemistry and aza-amino acids with heteroatomic side chains, J.Comb.Chem., 7, 864-878 (2005).
184. E. Wieczerzak, S. Rodziewicz-Motowidlo, E. Jankowska, A. Gieldon and J. Ciarkowski, An enormously active and selective azapeptide inhibitor of cathespin B, J.Pept.Sci., 13, 536-543 (2007).
185. R. J. Simon, R. S. Kania, R. N. Zuckermann, V. D. Huebner, D. A. Jewell, S. Banville, S. Ng, L. Wang, S. Rosenberg, C. K. Marlowe, D. C. Spellmeyer, R. Y. Tan, A. D. Frankel, D. V. Santi, F. E. Cohen and P. A. Bartlett, Peptoids - A modular approach to drug discovery, P.Natl.Acad.Sci.USA, 89, 9367-9371 (1992).
186. J. A. Patch, K. Kirshenbaum, S. L. Seurynck, R. N. Zuckermann and A. E. Barron, Versatile Oligo(N-Substituted) Glycines: The Many Roles of Peptoids in Drug Discovery, In: Pseudo-Peptides in Drug Discovery, 2004, ch. 1, 1-31.
187. Q. Sui, D. Borchardt and D. L. Rabenstein, Kinetics and equilibria of cis/trans isomerization of backbone amide bonds in peptoids, J.Am.Chem.Soc., 129, 12042-12048 (2007).
188. J. A. Patch and A. E. Barron, Helical peptoid mimics of magainin-2 amide, J.Am.Chem.Soc., 125, 12092-12093 (2003).
189. C. W. Wu, K. Kirshenbaum, T. J. Sanborn, J. A. Patch, K. Huang, K. A. Dill, R. N. Zuckermann and A. E. Barron, Structural and spectroscopic studies of peptoid oligomers with alpha-chiral aliphatic side chains, J.Am.Chem.Soc., 125, 13525- 13530 (2003).
190. T. S. Burkoth, A. T. Fafarman, D. H. Charych, M. D. Connolly and R. N. Zuckermann, Incorporation of unprotected heterocyclic side chains into peptoid oligomers via solid-phase submonomer synthesis, J.Am.Chem.Soc., 125, 8841- 8845 (2003).
191. J. M. Holub, H. J. Jang and K. Kirshenbaum, Clickity-click: highly functionalized peptoid oligomers generated by sequential conjugation reactions on solid-phase support, Org.Biomol.Chem., 4, 1497-1502 (2006).
192. J. R. Holder, R. M. Bauzo, Z. M. Xiang, J. Scott and C. Haskell-Luevano, Design and pharmacology of peptoids and peptide-peptoid hybrids based on the melanocortin agonists core tetrapeptide sequence, Bioorg.Med.Chem.Lett., 13, 4505- 4509 (2003).
193. R. Ruijtenbeek, J. A. W. Kruijtzer, W. van de Wiel, M. J. E. Fischer, M. Fluck, F. A. M. Redegeld, R. M. J. Liskamp and F. P. Nijkamp, Peptoid-peptide hybrids that bind Syk SH2 domains involved in signal transduction, ChemBioChem, 2, 171-179 (2001).
194. J. A. W. Kruijtzer, W. A. J. Nijenhuis, N. Wanders, W. H. Gispen, R. M. J. Liskamp and R. A. H. Adan, Peptoid-peptide hybrids as potent novel melanocortin receptor ligands, J.Med.Chem., 48, 4224-4230 (2005).
195. C. Gilon, M. A. Dechantsreiter, F. Burkhart, A. Friedler and H. Kessler, Synthesis of N-Alkylated Peptides, In Houben-Weyl. Methods of Organic Chemistry. Synthesis of Peptides and Peptidomimetics., 4th edn., 2003, vol. E22c, ch. 10.1, 262.
196. G. Calo, A. Rizzi, D. Rizzi, R. Bigoni, R. Guerrini, G. Marzola, M. Marti, J. McDonald, M. Morari, D. G. Lambert, S. Salvadori and D. Regoli, [Nphe(1),Arg(14),Lys(15)]nociceptin-NH2, a novel potent and selective antagonist of the nociceptin/orphanin FQ receptor, Brit.J.Pharmacol., 136, 303-311 (2002).
197. R. C. Elgersma, G.E. Mulder, J. A. W. Kruijtzer, G. Posthuma, D. T. S. Rijkers and R. M. J. Liskamp, Transformation of the amyloidogenic peptide amylin(20-29) into its corresponding peptoid and retropeptoid: Access to both an amyloid inhibitor and template for self-assembled supramolecular tapes, Bioorg.Med.Chem.Lett., 17, 1837-1842 (2007).
198. D. J. Combs and R. S. Lokey, Extended peptoids: a new class of oligomers based on aromatic building blocks, Tetrahedron Lett., 48, 2679-2682 (2007).
199. O. Busnel, L. R. Bi, H. Dali, A. Cheguillaume, S. Chevance, A. Bondon, S. Muller and M. Baudy-Floc'h, Solid-phase synthesis of 'mixed' peptidomimetics using Fmoc-protected aza-/beta(3)-amino acids and alpha-amino acids, J.Org.Chem., 70, 10701-10708 (2005).
200. A. Cheguillaume, F. Lehardy, K. Bouget, M. Baudy-Floc'h and P. Le Grel, Submonomer solution synthesis of hydrazinoazapeptoids, a new class of pseudopeptides, J.Org.Chem., 64, 2924-2927 (1999).
201. J. A. Patch and A. E. Barron, Mimicry of bioactive peptides via non-natural, sequencespecific peptidomimetic oligomers, Curr.Opin.Chem.Biol., 6, 872-877 (2002).
202. D. Seebach, A. K. Beck and D. J. Bierbaum, The world of beta- and gamma-peptides comprised of homologated proteinogenic amino acids and other components, Chem.Biodivers., 1, 1111-1239 (2004).
203. C. Grison, S. Geneve, S. Claudel, P. Coutrot and M. Marraud, Catalytic hydrogenation of vinylogous peptides: a route towards gamma-peptide foldamers, Tetrahedron Lett., 44, 2297-2300 (2003).
204. C. Baldauf, R. Gunther and H. J. Hofmann, Delta-peptides and delta-amino acids as tools for peptide structure design - A theoretical study, J.Org.Chem., 69, 6214- 6220 (2004).
205. A. Violette, M.C. Verlant-Petit, V. Semetey, C. Hemmerlin, R. Casimir, R. Graff, M. Marraud, J. P. Briand, D. Rognan and G. Guichard, N,N0-linked oligoureas as foldamers: Chain length requirements for helix formation in protic solvent investigated by circular dichroism, NMR spectroscopy, and molecular dynamics, J.Am.Chem.Soc., 127, 2156-2164 (2005).
206. A. Boeijen, J. van Ameijde and R. M. J. Liskamp, Solid-phase synthesis of oligourea peptidomimetics employing the Fmoc protection strategy, J.Org.Chem., 66, 8454- 8462 (2001).
207. A. Wiszniewska, D. Kunce, N. N. Chung, P. W. Schiller and J. Izdebski, p-Nitrophenoxycarbonyl derivatives of Boc-protected diaminoalkanes in the synthesis of enkephalin peptidomimetics, J.Pept.Sci., 11, 579-583 (2005).
208. C. Y. Cho, C. W. Liu, D. E. Wemmer and P. G. Schultz, Cyclic and linear oligocarbamate ligands for human thrombin, Bioorg.Med.Chem., 7, 1171-1179 (1999).
209. J. Venkatraman, S. C. Shankaramma and P. Balaram, Design of folded peptides, Chem.Rev., 101, 3131-3152 (2001).
210. W. A. Loughlin, J. D. A. Tyndall, M. P. Glenn and D. P. Fairlie, Beta-strand mimetics, Chem.Rev., 104, 6085-6117 (2004).
211. J. D. A. Tyndall, T. Nall and D. P. Fairlie, Proteases universally recognize beta strands in their active sites, Chem.Rev., 105, 973-999 (2005).
212. M. J. Pérez de Vega, M. Martin-Martinez and R. Gonzalez-Mun{ogonek} iz, Modulation of protein-protein interactions by stabilizing/mimicking protein secondary structure elements, Curr.Top.Med.Chem., 7, 33-62 (2007).
213. T. Moriuchi and T. Hirao, Highly ordered structures of peptides by using molecular scaffolds, Chem.Soc.Rev., 33, 294-301 (2004).
214. K. Y. Tsang, H. Diaz, N. Graciani and J. W. Kelly, Hydrophobic cluster formation is necessary for dibenzofuran-based amino acids to function as b-sheet nucleators, J.Am.Chem.Soc., 116, 3988-4005 (1994).
215. C. L. Nesloney and J. W. Kelly, A 2,30-substituted biphenyl-based amino acid facilitates the formation of a monomeric beta-hairpin-like structure in aqueous solution at elevated temperature, J.Am.Chem.Soc., 118, 5836-5845 (1996).
216. K. H. Mayo, R. P. M. Dings, C. Flader, I. Nesmelova, B. Hargittai, D. W. J. van der Schaft, L. I. van Eijk, D. Walek, J. Haseman, T. R. Hoye and A. W. Griffioen, Design of a partial peptide mimetic of anginex with antiangiogenic and anticancer activity, J.Biol.Chem., 278, 45746-45752 (2003).
217. M. C. Song, S. Rajesh, Y. Hayashi and Y. Kiso, Design and synthesis of new inhibitors of HIV-1 protease dimerization with conformationally constrained templates, Bioorg.Med.Chem.Lett., 11, 2465-2468 (2001).
218. V. Brandmeier, W. H. B. Sauer and M. Feigel, Antiparallel beta-sheet conformation in cyclopeptides containing a pseudo-amino acid with a biphenyl moiety, Helv.Chim.Acta, 77, 70-85 (1994).
219. E. Perissutti, F. Frecentese, A. Lavecchia, F. Fiorino, B. Severino, F. De Angelis, V. Santagada and G. Caliendo, Design and synthesis of potential beta-sheet nucleators via Suzuki coupling reaction, Tetrahedron, 63, 12779-12785 (2007).
220. M. Erdelyi, V. Langer, A. Karlen and A. Gogoll, Insight into beta-hairpin stability: a structural and thermodynamic study of diastereomeric beta-hairpin mimetics, New J.Chem., 26, 834-843 (2002).
221. D. S. Kemp and Z. Q. Li, 2-amino-20-carboxydiphenylacetylenes as beta-turn mimetics - Synthesis and conformational properties, Tetrahedron Lett., 36, 4175-4178 (1995).
222. K. Kim and J. P. Germanas, Peptides constrained to type VI beta-turns. 2. Antiparallel beta-ladder formation, J.Org.Chem., 62, 2853-2860 (1997).
223. J. A. Robinson, The design, synthesis and conformation of some new beta-hairpin mimetics: Novel reagents for drug and vaccine discovery, Synlett., 429-441 (2000).
224. Y. Che, B. R. Brooks and G. R. Marshall, Development of small molecules designed to modulate protein-protein interactions., J.Comput.Aid.Mol.Des., 20, 109-130 (2006).
225. B. R. Huck, J. D. Fisk and S. H. Gellman, Promotion of sheet formation in alphapeptide strands by a beta-peptide reverse turn, Org.Lett., 2, 2607-2610 (2000).
226. B. H. Baek, M. R. Lee, K. Y. Kim, U. I. Cho, D. W. Boo and I. Shin, Di-oxanipecotic acids as more stable turn motifs than di-nipecotic acids, Tetrahedron Lett., 44, 3447-3450 (2003).
227. J. P. Schneider and J. W. Kelly, Synthesis and efficacy of square-planar coppercomplexes designed to nucleate beta-sheet structure, J.Am.Chem.Soc., 117, 2533- 2546 (1995).
228. M. North, Incorporation of conformationally constrained beta-amino acids into peptides, J.Pept.Sci., 6, 301-313 (2000).
229. C. P. R. Hackenberger, I. Schiffers, J. Runsink and C. Bolm, General synthesis of unsymmetrical norbornane scaffolds as inducers for hydrogen bond interactions in peptides, J.Org.Chem., 69, 739-743 (2004).
230. J. Fotins and D. B. Smithrud, Creation and investigation of protein-core mimetics with parallel and antiparallel aligned amino acids, J.Org.Chem., 70, 4452-4459 (2005).
231. K. Ryan, L. J. Gershell and W. C. Still, A synthetic receptor motif designed for extended peptide conformations, Tetrahedron, 56, 3309-3318 (2000).
232. F. Freire, J. D. Fisk, A. J. Peoples, M. Ivancic, I. A. Guzei and S. H. Gellman, Diacid linkers that promote parallel b-sheet secondary structure in water, J.Am.Chem.Soc., 130, 7839-7841(2008).
233. J. D. Fisk, M. A. Schmitt and S. H. Gellman, Thermodynamic analysis of autonomous parallel beta-sheet formation in water, J.Am.Chem.Soc., 128, 7148-7149 (2006).
234. D. S. Kemp and B. R. Bowen, Synthesis of peptide-functionalized diacylaminoepindolidiones as template for b-sheet formation, Tetrahedron Lett., 29, 5077-5080 (1988).
235. W. F. Michne and J. D. Schroeder, Design and synthesis of a beta-strand inducer - Application to ICAM-1/LFA-1 mediated cellular adhesion, Int. J. Peptide Protein Res., 47, 2-8 (1996).
236. C. Bonauer, M. Zabel and B. Konig, Synthesis and peptide binding properties of methoxypyrrole amino acids (MOPAS), Org.Lett., 6, 1349-1352 (2004).
237. J. S. Nowick, What I have learned by using chemical model systems to study biomolecular structure and interactions, Org.Biomol.Chem., 4, 3869-3885 (2006).
238. R. J. Woods, J. O. Brower, E. Castellanos, M. Hashemzadeh, O. Khakshoor, W. A. Russu and J. S. Nowick, Cyclic modular beta-sheets, J.Am.Chem.Soc., 129, 2548-2558 (2007).
239. S. Levin and J. S. Nowick, An artificial beta-sheet that dimerizes through parallel b-sheet interactions, J.Am.Chem.Soc., 129, 13043-13048 (2007).
240. L. Belvisi, C. Gennari, A. Mielgo, D. Potenza and C. Scolastico, Conformational preferences of peptides containing reverse-turn mimetic bicyclic lactams: Inverse gamma-turns versus type-II 0 beta-turns - Insights into beta-hairpin stability, Eur.J.Org.Chem., 389-400 (1999).
241. J. A. Robinson, b-Hairpin peptidomimetics: design, structures and biological activities, Accounts Chem.Res., ASAP, (2008).
242. A. Descours, K.Moehle, A. Renard and J. A. Robinson, A new family of beta-hairpin mimetics based on a trypsin inhibitor from sunflower seeds, ChemBioChem, 3, 318- 323 (2002).
243. S. J. DeMarco, H. Henze, A. Lederer, K. Moehle, R. Mukherjee, B. Romagnoli, J. A. Robinson, F. Brianza, F. O. Gombert, S. Lociuro, C. Ludin, J. W. Vrijbloed, J. Zumbrunn, J. P. Obrecht, D. Obrecht, V. Brondani, F. Hamy and T. Klimkait, Discovery of novel, highly potent and selective beta-hairpin mimetic CXCR4 inhibitors with excellent anti-HIV activity and pharmacokinetic profiles, Bioorg.Med.Chem., 14, 8396-8404 (2006).
244. J. A. Robinson, S. C. Shankaramma, P. Jettera, U. Kienzl, R. A. Schwendener, J. W. Vrijbloed and D. Obrecht, Properties and structure-activity studies of cyclic beta-hairpin peptidomimetics based on the cationic antimicrobial peptide protegrin I, Bioorg.Med.Chem., 13, 2055-2064 (2005).
245. R. L. A. Dias, R. Fasan, K. Moehle, A. Renard, D. Obrecht and J. A. Robinson, Protein ligand design: From phage display to synthetic protein epitope mimetics in human antibody Fc-binding peptidomimetics, J.Am.Chem.Soc., 128, 2726-2732 (2006).
246. Z. Athanassiou, K. Patora, R. L. A. Dias, K. Moehle, J. A. Robinson and G. Varani, Structure-guided peptidomimetic design leads to nanomolar beta-hairpin inhibitors of the Tat-TAR interaction of bovine immunodeficiency Virus, Biochemistry, 46, 741-751 (2007).
247. K. Moehle, Z. Athanassiou, K. Patora, A. Davidson, G. Varani and J. A. Robinson, Design of beta-hairpin peptidomimetics that inhibit binding of alpha-helical HIV-1 rev protein to the rev response element RNA, Angew.Chem.Int.Edit., 46, 9101- 9104 (2007).
248. R. Fasan, R. L. A. Dias, K. Moehle, O. Zerbe, J. W. Vrijbloed, D. Obrecht and J. A. Robinson, Using a beta-hairpin to mimic an alpha-helix: Cyclic peptidomimetic inhibitors of the p53-HDM2 protein-protein interaction, Angew.Chem.Int.Edit., 43, 2109-2112 (2004).
249. N. Srinivas, K. Moehle, K. bou-Hadeed, D. Obrecht and J. A. Robinson, Biaryl amino acid templates in place of D-Pro-L-Pro in cyclic b-hairpin cationic antimicrobial peptidomimetics, Org.Biomol.Chem., 5, 3100-3105 (2007).
250. J. D. A. Tyndall and D. P. Fairlie, Macrocycles mimic the extended peptide conformation recognized by aspartic, serine, cysteine and metallo proteases, Curr.Med.Chem., 8, 893-907 (2001).
251. R. C. Reid, M. J. Kelso, M. J. Scanlon and D. P. Fairlie, Conformationally constrained macrocycles that mimic tripeptide beta-strands in water and aprotic solvents, J.Am.Chem.Soc., 124, 5673-5683 (2002).
252. M. P. Glenn, L. K. Pattenden, R. C. Reid, D. P. Tyssen, J. D. A. Tyndall, C. J. Birch and D. P. Fairlie, beta-strand mimicking macrocyclic amino acids: Templates for protease inhibitors with antiviral activity, J.Med.Chem., 45, 371-381 (2002).
253. C. B. Xue, M. E. Voss, D. J. Nelson, J. J. W. Duan, R. J. Cherney, I. C. Jacobson, X. H. He, J. Roderick, L. H. Chen, R. L. Corbett, L. Wang, D. T. Meyer, K. Kennedy, W. F. DeGrado, K. D. Hardman, C. A. Teleha, B. D. Jaffee, R. Q. Liu, R. A. Copeland, M. B. Covington, D. D. Christ, J. M. Trzaskos, R. C. Newton, R. L. Magolda, R. R. Wexler and C. P. Decicco, Design, synthesis, and structure-activity relationships of macrocyclic hydroxamic acids that inhibit tumor necrosis factor alpha release in vitro and in vivo, J.Med.Chem., 44, 2636- 2660 (2001).
254. G. Abbenante, D. A. Bergman, R. I. Brinkworth, D. R. March, R. C. Reid, P. A. Hunt, I. W. James, R. J. Dancer, B. Garnham, M. L. Stoermer and D. P. Fairlie, Structure-activity relationships for macrocyclic peptidomimetic inhibitors of HIV-1 protease, Bioorg.Med.Chem.Lett., 6, 2531-2536 (1996).
255. K. Ersmark, M. Nervall, H. Gutierrez-de-Teran, E. Hamelink, L. K. Janka, J. C. Clemente, B. M. Dunn, A. Gogoll, B. Samuelsson, J. Aqvist and A. Hallberg, Macrocyclic inhibitors of the malarial aspartic proteases plasmepsin I, II, and IV, Bioorgan.Med.Chem., 14, 2197-2208 (2006).
256. S. J. Stachel, C. A. Coburn, S. Sankaranarayanan, E. A. Price, B. L. Pietrak, Q. Huang, J. Lineberger, A. S. Espeseth, L. X. Jin, J. Ellis, M. K. Holloway, S. Munshi, T. Allison, D. Hazuda, A. J. Simon, S. L. Graham and J. P. Vacca, Macrocyclic inhibitors of beta-secretase: Functional activity in an animal model, J.Med.Chem., 49, 6147-6150 (2006).
257. A. K. Ghosh, T. Devasamudram, L. Hong, C. DeZutter, X. M. Xu, V. Weerasena, G. Koelsch, G. Bilcer and J. Tang, Structure-based design of cycloamide-urethanederived novel inhibitors of human brain memapsin 2 (beta-secretase), Bioorg.Med.Chem.Lett., 15, 15-20 (2005).
258. Y. S. Tsantrizos, J. M. Ferland, A. McClory, M. Poirier, V. Farina, N. K. Yee, X. J. Wang, N. Haddad, X. D. Wei, J. H. Xu and L. Zhang, Olefin ring-closing metathesis as a powerful tool in drug discovery and development - potent macrocyclic inhibitors of the hepatitis C virus NS3 protease, J.Organomet.Chem., 691, 5163-5171 (2006).
259. N. Goudreau, C. Brochu, D. R. Cameron, J. S. Duceppe, A. M. Faucher, J. M. Ferland, C. Grand-Maitre, M. Poirier, B. Simoneau and Y. S. Tsantrizos, Potent inhibitors of the hepatitis C virus NS3 protease: Design and synthesis of macrocyclic substrate-based beta-strand mimics, J.Org.Chem., 69, 6185-6201 (2004).
260. A. B. Smith III, M. C. Guzman, P. A. Sprengeler, T. P. Keenan, R. C. Holcomb, J. L. Wood, P. J. Carroll and R. Hirschmann, De novo design, synthesis and X-ray crystal structures of pyrrolinone-based b-strand peptidomimetics, J.Am.Chem.Soc., 116, 9947-9962 (1994).
261. A. B. Smith, R. Hirschmann, A. Pasternak, R. Akaishi, M. C. Guzman, D. R. Jones, T. P. Keenan, P. A. Sprengeler, P. L. Darke, E. A. Emini, M. K. Holloway and W. A. Schleif, Design and synthesis of peptidomimetic inhibitors of HIV-1 protease and renin - Evidence for improved transport, J.Med.Chem., 37, 215-218 (1994).
262. A. B. Smith, T. Nittoli, P. A. Sprengeler, J. J. W. Duan, R. Q. Liu and R. F. Hirschmann, Design, synthesis, and evaluation of a pyrrolinone-based matrix metalloprotease inhibitor, Org.Lett., 2, 3809-3812 (2000).
263. K. H. Lee, G. L. Olson, D. R. Bolin, A. B. Benowitz, P. A. Sprengeler, A. B. Smith, R. F. Hirschmann and D. C. Wiley, The crystal structure of a pyrrolinone-peptide hybrid ligand bound to the human class II MHC protein HLA-DR1, J.Am.Chem.Soc., 122, 8370-8375 (2000).
264. A. B. Smith, A. K. Charnley, E. F. Mesaros, O. Kikuchi, W. Y. Wang, A. Benowitz, C. L. Chu, J. J. Feng, K. H. Chen, A. Lin, F. C. Cheng, L. Taylor and R. Hirschmann, Design, synthesis, and binding affinities of pyrrolinone-based somatostatin mimetics, Org.Lett., 7, 399-402 (2005).
265. S. T. Philips, M. Rezac, U. Abel, M. Kossenjans and P. A. Bartlett, '@-tides': The 1,2-dihydro-3(6H)-pyridinone unit as a b-strand mimic, J.Am.Chem.Soc., 124, 58-59 (2002).
266. S. T. Phillips, L. K. Blasdel and P. A. Bartlett, @-tides as reporters for molecular associations, J.Am.Chem.Soc., 127, 4193-4198 (2005).
267. M. C. Hammond, B. Z. Harris, W. A. Lim and P. A. Bartlett, beta strand peptidomimetics as potent PDZ domain ligands, Chem.Biol., 13, 1247-1251 (2006).
268. M. C. Hammond and P. A. Bartlett, Synthesis of amino acid-derived cyclic acyl amidines for use in beta-strand peptidomimetics, J.Org.Chem., 72, 3104-3107 (2007).
269. D. Blomberg, K. Brickmann and J. Kihlberg, Synthesis of a beta-strand mimetic based on a pyridine scaffold, Tetrahedron, 62, 10937-10944 (2006).
270. Y. M. Qian, M. A. Blaskovich, M. Saleem, C. M. Seong, S. P. Wathen, A. D. Hamilton and S. M. Sebti, Design and structural requirements of potent peptidomimetic inhibitors of P21(Ras) farnesyltransferase, J.Biol.Chem., 269, 12410- 12413 (1994).
271. Y. M. Qian, A. Vogt, S. M. Sebti and A. D. Hamilton, Design and synthesis of nonpeptide Ras CAAX mimetics as potent farnesyltransferase inhibitors, J.Med.Chem., 39, 217-223 (1996).
272. G. Semple, D. M. Ashworth, G. R. Baker, A. R. Batt, A. J. Baxter, D. W. M. Benzies, L. H. Elliot, D. M. Evans, R. J. Franklin, P. Hudson, P. D. Jenkins, G. R. Pitt, D. P. Rooker, A. Sheppard, M. SZELKE, S. Yamamoto and Y. Isomura, Pyridonebased peptidomimetic inhibitors of interleukin-1 beta-converting enzyme (ICE), Bioorg.Med.Chem.Lett., 7, 1337-1342 (1997).
273. J. M. C. Golec, M. D. Mullican, M. A. Murcko, K. P. Wilson, D. P. Kay, S. D. Jones, R. Murdoch, G. W. Bemis, S. A. Raybuck, Y. P. Luong and D. J. Livingston, Structure-based design of non-peptidic pyridone aldehydes as inhibitors of interleukin-1 beta converting enzyme, Bioorg.Med.Chem.Lett., 7, 2181-2186 (1997).
274. F. J. Brown, D. W. Andisik, P. R. Bernstein, C. B. Bryant, C. Ceccarelli, J. R. Damewood, S. A. Woolson, P. D. Edwards, R. A. Earley, S. Feeney, R. C. Green, B. Gomes, B. J. Kosmider, R. D. Krell, A. Shaw, G. B. Steelman, R. N. Thomas, E. P. Vacek, C. A. Veale, P. A. Tuthill, P. Warner, J. C. Williams and D. J. Wolanin, Design of orally-active, nonpeptidic inhibitors of human-leukocyte elastase, J.Med.Chem., 37, 1259-1261 (1994).
275. R. M. Freidinger, D. F. Veber, D. S. Perlow, J. R. Brooks and R. Saperstein, Bioactive conformation of luteinizing-hormone-releasing hormone - evidence from a conformationally constrained analogue, Science, 210, 656-658 (1980).
276. A. Perdih and D. Kikelj, The application of Freidinger lactams and their analogues in the design of conformationally constrained peptidomimetics, Curr.Med.Chem., 13, 1525-1556 (2006).
277. J. Cluzeau and W. D. Lubell, Design, synthesis, and application of azabicyclo[X.Y.O]alkanone amino acids as constrained dipeptide surrogates and peptide mimics, Biopolymers, 80, 98-150 (2005).
278. P. D. Boatman, C. O. Ogbu, M. Eguchi, H. O. Kim, H. Nakanishi, B. L. Cao, J. P. Shea and M. Kahn, Secondary structure peptide mimetics: Design, synthesis, and evaluation of beta-strand mimetic thrombin inhibitors, J.Med.Chem., 42, 1367-1375 (1999).
279. W. A. Slusarchyk, J. A. Robl, P. C. Taunk, M. M. Asaad, J. E. Bird, J. Dimarco and Y. Pan, Dual metalloprotease inhibitors. 5. Utilization of bicyclic azepinonethiazolidines and azepinonetetrahydrothiazines in constrained peptidomimetics of mercaptoacyl dipeptides, Bioorg.Med.Chem.Lett., 5, 753-758 (1995).
280. X. M. Chen, R. P. M. Dings, I. Nesmelova, S. Debbert, J. R. Haseman, J. Maxwell, T. R. Hoye and K. H. Mayo, Topomimetics of amphipathic beta-sheet and helixforming bactericidal peptides neutralize lipopolysaccharide endotoxins, J.Med.Chem., 49, 7754-7765 (2006).
281. R. P. M. Dings, X. M. Chen, D. M. E. I. Hellebrekers, L. I. van Eijk, Y. Zhang, T. R. Hoye, A. W. Griffioen and K. H. Mayo, Design of nonpeptidic topomimetics of antiangiogenic proteins with antitumor activities, J.Natl.Cancer Inst., 98, 932-936 (2006).
282. H. Yin and A. D. Hamilton, Strategies for targeting protein-protein interactions with synthetic agents, Angew.Chem.Int.Edit., 44, 4130-4163 (2005).
283. Y. Wei, G. L. McLendon, A. D. Hamilton, M. A. Case, C. B. Purring, Q. Lin, H. S. Park, C. S. Lee and T. N. Yu, Disruption of protein-protein interactions: design of a synthetic receptor that blocks the binding of cytochrome c to cytochrome c peroxidase, Chem.Commun., 1580-1581 (2001).
284. F. Z. Zhang, O. Sadovski, S. J. Xin and G. A. Woolley, Stabilization of folded peptide and protein structures via distance matching with a long, rigid cross-linker, J.Am.Chem.Soc., 129, 14154 ff. (2007).
285. A. K. Boal, I. Guryanov, A. Moretto, M. Crisma, E. L. Lanni, C. Toniolo, R. H. Grubbs and D.J. O'Leary, Facile and E-selective intramolecular ring-closing metathesis reactions in 3(10)-helical peptides: A 3D structural study, J.Am.Chem.Soc., 129, 6986 ff. (2007).
286. J. Garner and M. M. Harding, Design and synthesis of alpha-helical peptides and mimetics, Org.Biomol.Chem., 5, 3577-3585 (2007).
287. J.-S. Park, H.-S. Lee, J. R. Lai, B. M. Kim and S. H. Gellman, Accommodation of a-substituted residues in the b-peptide 12-helix: expanding the range of substitution patterns available to a foldamer scaffold, J.Am.Chem.Soc., 125, 8539-8545 (2003).
288. C. Baldauf, R. Gunther and H. J. Hofmann, Control of helix formation in vinylogous gamma-peptides by (E)- and (Z)-double bonds: A way to ion channels and monomolecular nanotubes, J.Org.Chem., 70, 5351-5361 (2005).
289. L. Zhao and J. Chmielewski, Inhibiting protein-protein interactions using designed molecules, Curr.Opin.Struct.Biol., 15, 31-34 (2005).
290. J. M. Davis, L. K. Tsou and A. D. Hamilton, Synthetic non-peptide mimetics of alpha-helices, Chem.Soc.Rev., 36, 326-334 (2007).
291. J. P. Schneider and J. W. Kelly, Templates that induce alpha-helical, beta-sheet, and loop conformations, Chem.Rev., 95, 2169-2187 (1995).
292. D. S. Kemp and T. P. Curran, (2S,5S,8S,11S)-1-Acetyl-1,4-diaza-3-keto-5-carboxy-10-thia-tricyclo-[2.8.04,8]-tridecane, 1 the preferred conformation of 1 (1=α-Temp-OH) and its peptide conjugates a-Temp-L-(Ala)n-OR (n=1 to 4) and a-Temp-L-Ala-LPhe-L-Lys(E-Boc)-L-Lys(E-Boc)-NHMe studies of templates for a-helix formation, Tetrahedron Lett., 29, 4935-4938 (1988).
293. T. Arrhenius and A. C. Satterthwait, The substitution of an amide-amide backbone hydrogen bond in an a-helical peptide with a covalent hydrogen bond mimic, In: Peptides: Chemistry, structure and biology, Proceedings of the 11th American Chemical Symposium, 870-872, 1990.
294. E. Cabezas and A. C. Satterthwait, The hydrogen bond mimic approach: Solidphase synthesis of a peptide stabilized as an alpha-helix with a hydrazone link, J.Am.Chem.Soc., 121, 3862-3875 (1999).
295. J. C. Calvo, K. C. Choconta, D. Diaz, O. Orozco, M. M. Bravo, F. Espejo, L. M. Salazar, F. Guzman and M. E. Patarroyo, An alpha helix conformationally restricted peptide is recognized by cervical carcinoma patients' sera, J.Med.Chem., 46, 5389-5394 (2003).
296. R. N. Chapman, G. Dimartino and P. S. Arora, A highly stable short alpha-helix constrained by a main-chain hydrogen-bond surrogate, J.Am.Chem.Soc., 126, 12252-12253 (2004).
297. R. N. Chapman and P. S. Arora, Optimized synthesis of hydrogen-bond surrogate helices: Surprising effects of microwave heating on the activity of grubbs catalysts, Org.Lett., 8, 5825-5828 (2006).
298. G. Dimartino, D. Y. Wang, R. N. Chapman and P. S. Arora, Solid-phase synthesis of hydrogen-bond surrogate-derived alpha-helices, Org.Lett., 7, 2389-2392 (2005).
299. D. Y. Wang, K. Chen, G. Dimartino and P. S. Arora, Nucleation and stability of hydrogen-bond surrogate-based alpha-helices, Org.Biomol.Chem., 4, 4074-4081 (2006).
300. D. Wang, K. Chen, J. L. Kulp and P. S. Arora, Evaluation of biologically relevant short alpha-helices stabilized by a main-chain hydrogen-bond surrogate, J.Am.Chem.Soc., 128, 9248-9256 (2006).
301. J. Liu, D. Wang, Q. Zheng, M. Lu and P. S. Arora, Atomic structure of a short alpha-helix stabilized by a main chain hydrogen-bond surrogate, J.Am.Chem.Soc., 130, 4334-4337 (2008).
302. D. Y. Wang, W. Liao and P. S. Arora, Binding properties of artificial a helices derived from a hydrogen-bond surrogate: Application to Bcl-xL, Angew.Chem.Int.Edit., 44, 6525-6529 (2005).
303. D. Wang, M. Lu and P. S. Arora, Inhibition of HIV-1 fusion by hydrogen-bondsurrogate-based alpha helices, Angew.Chem.Int.Edit., 47, 1879-1882 (2008).
304. C. A. Hutton and P. A. Bartlett, Preparation of diazabicyclo[4.3.0]nonene-based peptidomimetics, J.Org.Chem., 72, 6865-6872 (2007).
305. R. E. Austin, R. A. Maplestone, A. M. Sefler, K. Liu, W. N. Hruzewicz, C. W. Liu, H. S. Cho, D. E. Wemmer and P. A. Bartlett, Template for stabilization of a peptide alpha-helix: Synthesis and evaluation of conformational effects by circular dichroism and NMR, J.Am.Chem.Soc., 119, 6461-6472 (1997).
306. D. C. Horwell, W. Howson, G. S. Ratcliffe and H. M. G. Willems, The design of dipeptide helical mimetics: The synthesis, tachykinin receptor affinity and conformational analysis of 1,1,6-trisubstituted indanes, Bioorgan.Med.Chem., 4, 33-42 (1996).
307. E. Jacoby, Biphenyls as potential mimetics of protein alpha-helix, Bioorg.Med.Chem.Lett., 12, 891-893 (2002).
308. B. P. Orner, J. T. Ernst and A. D. Hamilton, Toward proteomimetics: Terphenyl derivatives as structural and functional mimics of extended regions of an alphahelix, J.Am.Chem.Soc., 123, 5382-5383 (2001).
309. H.Yin,G. Lee,K.A. Sedey,O.Kutzki,H. S. Park, B. P.Orner, J. T. Ernst,H.G.Wang, S. M. Sebti and A. D. Hamilton, Terphenyl-based bak BH3 a-helical proteomimetics as low-molecular-weight antagonists of Bcl-xL, J.Am.Chem.Soc., 127, 10191-10196 (2005).
310. O. Kutzki, H. S. Park, J. T. Ernst, B. P. Orner, H. Yin and A. D. Hamilton, Development of a potent Bcl-xL antagonist based on alpha-helix mimicry, J.Am.Chem.Soc., 124, 11838-11839 (2002).
311. H. Yin, G. I. Lee, H. S. Park, G. A. Payne, J. M. Rodriguez, S. M. Sebti and A. D. Hamilton, Terphenyl-based helical mimetics that disrupt the p53/HDM2 interaction, Angew.Chem.Int.Edit., 44, 2704-2707 (2005).
312. J. T. Ernst, O. Kutzki, A. K. Debnath, S. Jiang, H. Lu and A. D. Hamilton, Design of a protein surface antagonist based on alpha-helix mimicry: Inhibition of gp41 assembly and viral fusion, Angew.Chem.Int.Edit., 41, 278 ff. (2001).
313. I. C. Kim and A. D. Hamilton, Diphenylindane-based proteomimetics reproduce the projection of the i, i {thorn} 3, i {thorn} 4, and i {thorn} 7 residues on an a-helix, Org.Lett., 8, 1751-1754 (2006).
314. J. T. Ernst, J. Becerril, H. S. Park, H. Yin and A. D. Hamilton, Design and application of an alpha-helix-mimetic scaffold based on an oligoamide-foldamer strategy: Antagonism of the bak BH3/Bcl-xL complex, Angew.Chem.Int.Edit., 42, 535 ff. (2003).
315. J. M. Ahn and S. Y. Han, Facile synthesis of benzamides to mimic an alpha-helix, Tetrahedron Lett., 48, 3543-3547 (2007).
316. H. Yin and A. D. Hamilton, Terephthalamide derivatives as mimetics of the helical region of Bak peptide target Bcl-xL protein, Bioorg.Med.Chem.Lett., 14, 1375- 1379 (2004).
317. J. M. Rodriguez and A. D. Hamilton, Intramolecular hydrogen bonding allows simple enaminones to structurally mimic the i, i {thorn} 4, and i {thorn}7 residues of an a-helix, Tetrahedron Lett., 47, 7443-7446 (2006).
318. A. Volonterio, L. Moisan and J. Julius, Synthesis of pyridazine-based scaffolds as alpha-helix mimetics, Org.Lett., 9, 3733-3736 (2007).
319. L. Moisan, S. Odermatt, N. Gombosuren, A. Carella and J. Rebek, Synthesis of an oxazole-pyrrole-piperazine scaffold as an alpha-helix mimetic, Eur. J. Org. Chem., 10, 1673-1676 (2008).
320. P. Maity and B. Konig, Synthesis and structure of 1,4-dipiperazino benzenes: Chiral terphenyl-type peptide helix mimetics, Org.Lett., 10, 1473-1476 (2008).
321. Y. Che, B. R. Brooks and G. R. Marshall, Protein recognition motifs: Design of peptidomimetics of helix surfaces, Biopolymers, 86, 288-297 (2007).
322. W. Antuch, S. Menon, Q. Z. Chen, Y. C. Lu, S. Sakamuri, B. Beck, V. Schauer-Vukasinovic, S. Agarwal, S. Hess and A. Domling, Design and modular parallel synthesis of a MCR derived alpha-helix mimetic protein-protein interaction inhibitor scaffold, Bioorg.Med.Chem.Lett., 16, 1740-1743 (2006).
323. H. Oguri, A. Oomura, S. Tanabe and M. Hirama, Design and synthesis of a transfused polycyclic ether skeleton as an a-helix mimetic scaffold, Tetrahedron Lett., 46, 2179-2183 (2005).
324. H. Oguri, S. Tanabe, A. Oomura, M. Umetsu and M. Hirama, Synthesis and evaluation of a-helix mimetics based on a trans-fused polycyclic ether: sequenceselective binding to aspartate pairs in a-helical peptides, Tetrahedron Lett., 47, 5801-5805 (2006).
325. S. E. Van Compernolle, A. V. Wiznycia, J. R. Rush, M. Dhanasekaran, P. W. Baures and S. C. Todd, Small molecule inhibition of hepatitis C virus E2 binding to CD81, Virology, 314, 371-380 (2003).
326. A. L. Rodriguez, A. Tamrazi, M. L. Collins and J. A. Katzenellenbogen, Design, synthesis, and in vitro biological evaluation of small molecule inhibitors of estrogen receptor a coactivator binding, J.Med.Chem., 47, 600-611 (2004).
327. J. S. Blakeney, R. C. Reid, G. T. Le and D. P. Fairlie, Nonpeptidic ligands for peptideactivated G protein-coupled receptors, Chem.Rev., 107, 2960-3041 (2007).
328. N. R. A. Beeley, Can peptides be mimicked?, Drug Discov.Today, 5, 354-363 (2000).
329. R. M. Jones, P. D. Boatman, G. Semple, Y.-J. Shin and S. Y. Tamura, Clinically validated peptides as template for de novo peptidomimetic drug design at G-proteincoupled receptors, Curr.Opin.Pharmacol., 3, 530-543 (2003).
330. A. Janecka, M. Zubrzycka and T. Janecki, Somatostatin analogues, J. Peptide Res., 58, 91-107 (2001).
331. L. Yang, Non-peptide Somatostatin Receptor Ligands, In: Annu. Rep. Med. Chem., 1999, ch. 21, 209-218.
332. R. M. Freidinger, Design and synthesis of novel bioactive peptides and peptidomimeties, J.Med.Chem., 46, 5553-5566 (2003).
333. R. H. Mattern, S. B. Moore, T. A. Tran, J. K. Rueter and M. Goodman, Synthesis, biological activities and conformational studies of somatostatin analogues, Tetrahedron, 56, 9819-9831 (2000).
334. V. Prasad, E. T. Birzin, C. T. McVaugh, R. D. van Rijn, S. P. Rohrer, G. Chicchi, D. J. Underwood, E. R. Thornton, A. B. Smith and R. Hirschmann, Effects of heterocyclic aromatic substituents on binding affinities at two distinct sites of somatostatin receptors. Correlation with the electrostatic potential of the substituents, J.Med.Chem., 46, 1858-1869 (2003).
335. R. Hirschmann, K. C. Nicolaou, S. Pietranico, J. Salvino, E. M. Leahy, P. A. Sprengeler, G. Furst, A. B. Smith, C. D. Strader, M. A. Cascieri, M. R. Candelore, C. Donaldson, W. Vale and L. Maechler, Nonpeptidal peptidomimetics with a beta-D-glucose scaffolding - A partial somatostatin agonist bearing a close structural relationship to a potent, selective substance-P antagonist, J.Am.Chem.Soc., 114, 9217-9218 (1992).
336. R. Hirschmann, J. Hynes, M.A. Cichy-Knight, R. D. van Rijn, P. A. Sprengeler, P. G. Spoors, W. C. Shakespeare, S. Pietranico-Cole, J. Barbosa, J. Liu, W. Q. Yao, S. Rohrer and A. B. Smith, Modulation of receptor and receptor subtype affinities using diastereomeric and enantiomeric monosaccharide scaffolds as a means to structural and biological diversity. A new route to ether synthesis, J.Med.Chem., 41, 1382-1391 (1998).
337. S. G. Gouin and P. V. Murphy, Synthesis of somatostatin mimetics based on the 1-deoxymannojirimycin scaffold, J.Org.Chem., 70, 8527-8532 (2005).
338. D. Damour, M. Barreau, J. C. Blanchard, M. C. Burgevin, A. Doble, F. Herman, G. Pantel, E. JamesSurcouf, M. Vuilhorgne, S. Mignani, L. Poitout, Y. LeMerrer and J. C. Depezay, Design, synthesis and binding affinities of novel non-peptide mimics of somatostatin/sandostatin_, Bioorg.Med.Chem.Lett., 6, 1667-1672 (1996).
339. B. P. Mowery, V. Prasad, C. S. Kenesky, A. R. Angeles, L. L. Taylor, J. J. Feng, W. L. Chen, A. Lin, F. C. Cheng, A. B. Smith and R. Hirschmann, Catechol: A minimal scaffold for non-peptide peptidomimetics of the i {thorn} 1 and i {thorn} 2 positions of the beta-turn of somatostatin, Org.Lett., 8, 4397-4400 (2006).
340. C. Papageorgiou and X. Borer, A non-peptide ligand for the somatostatin receptor having a benzodiazepinone structure, Bioorg.Med.Chem.Lett., 6, 267-272 (1996).
341. D. Damour, F. Herman, R. Labaudiniere, G. Pantel, M. Vuilhorgne and S. Mignani, Synthesis of novel proline and gamma-lactam derivatives as non-peptide mimics of Somatostatin/Sandostatin_, Tetrahedron, 55, 10135-10154 (1999).
342. D. Damour, M. Barreau, J. C. Blanchard, M. C. Burgevin, A. Doble, G. Pantel, R. Labaudiniere and S. Mignani, Synthesis and binding affinities of novel spirocyclic lactam peptidomimetics of somatostatin, Chem.Lett., 943-944 (1998).
343. A. J. Souers, A. A. Virgilio, A. Rosenquist, W. Fenuik and J. A. Ellman, Identification of a potent heterocyclic ligand to somatostatin receptor subtype 5 by the synthesis and screening of beta-turn mimetic libraries, J.Am.Chem.Soc., 121, 1817-1825 (1999).
344. D. Chianelli, Y. C. Kim, D. Lvovskiy and T. R. Webb, Application of a novel design paradigm to generate general nonpeptide combinatorial scaffolds mimicking beta turns: Synthesis of Ligands for somatostatin receptors, Bioorg.Med.Chem., 11, 5059-5068 (2003).
345. S. P. Rohrer, E. T. Birzin, R. T. Mosley, S. C. Berk, S. M. Hutchins, D. M. Shen, Y. S. Xiong, E. C. Hayes, R. M. Parmar, F. Foor, S. W. Mitra, S. J. Degrado, M. Shu, J. M. Klopp, S. J. Cai, A. Blake, W. W. S. Chan, A. Pasternak, L. H. Yang, A. A. Patchett, R. G. Smith, K. T. Chapman and J. M. Schaeffer, Rapid identification of subtype-selective agonists of the somatostatin receptor through combinatorial chemistry, Science, 282, 737-740 (1998).
346. L. H. Yang, S. C. Berk, S. P. Rohrer, R. T. Mosley, L. Q. Guo, D. J. Underwood, B. H. Arison, E. T. Birzin, E. C. Hayes, S. W. Mitra, R. M. Parmar, K. Cheng, T. J. Wu, B. S. Butler, F. Foor, A. Pasternak, Y. P. Pan, M. Silva, R. M. Freidinger, R. G. Smith, K. Chapman, J. M. Schaeffer and A. A. Patchett, Synthesis and biological activities of potent peptidomimetics selective for somatostatin receptor subtype 2, P.Natl.Acad.Sci.USA, 95, 10836-10841 (1998).
347. A. Pasternak, Y. Pan, R. T. Mosley, S. P. Rohrer, E. T. Birzin, J. M. Schaeffer, A. A. Patchett and L. Yang, Diverse peptidyl privileged structures as potent somatostatin receptor ligands, Lett. Drug Des. Discov., 1, 121-125 (2004).
348. S. P. Rohrer and J. M. Schaeffer, Identification and characterization of subtype selective somatostatin receptor agonists, J.Physiol.-Paris, 94, 211-215 (2000).
349. D. Feytens, M. De Vlaeminck, R. Cescato, D. Tourwe, J. C. Reubi, Highly potent 4-amino-indola[2,3-c]azepin-3-one-containig Somatostatin mimetics with a range of sst receptor selectivities, J. Med. Chem, 52, 95-104 (2009).
350. M. Ankersen, M. Crider, S. Q. Liu, B. Ho, H. S. Andersen and C. Stidsen, Discovery of a novel non-peptide somatostatin agonist with SST4 selectivity, J.Am.Chem.Soc., 120, 1368-1373 (1998).
351. M.O. Contour-Galcera, A. Sidhu, P. Plas and P. Roubert, 3-Thio-1,2,4-triazoles, novel somatostatin sst(2)/sst(5) agonists, Bioorg.Med.Chem.Lett., 15, 3555-3559 (2005).
352. H. Mabuchi, N. Suzuki and T. Miki, WO98/47882, 1998.
353. B. A. Hay, B. M. Cole, F. DiCapua, G. W. Kirk, M. C. Murray, R. A. Nardone, D. J. Pelletier, A. P. Ricketts, A. S. Robertson and T. W. Siegel, Small molecule somatostatin receptor subtype-2 antagonists, Bioorg.Med.Chem.Lett., 11, 2731- 2734 (2001).
354. R. E. Martin, L. G. Green, W. Guba, N. Kratochwil and A. Christ, Discovery of the first nonpeptidic, small-molecule, highly selective somatostatin receptor subtype 5 antagonists: A chemogenomics approach, J.Med.Chem., 50, 6291-6294 (2007).
355. L. Poitout, P. Roubert, M.O. Contour-Galera, C. Moinet, J. Lannoy, J. Pommier, P. Plas, D. Bigg and C. Thurieau, Identification of potent non-peptide somatostatin antagonists with sst(3) selectivity, J.Med.Chem., 44, 2990-3000 (2001).
356. D. Seebach, L. Schaeffer, M. Brenner and D. Hoyer, Design and synthesis of gamma-dipeptide derivatives with submicromolar affinities for human somatostatin receptors, Angew.Chem.Int.Edit., 42, 776-778 (2003).
357. D. Seebach, M. Rueping, P. I. Arvidsson, T. Kimmerlin, P. Micuch, C. Noti, D. Langenegger and D. Hoyer, Linear, peptidase-resistant beta(2)/beta(3)-di- and alpha/beta(3)-tetrapeptide derivatives with nanomolar affinities to a human somatostatin receptor -Helv.Chim.Acta, 84, 3503-3510 (2001).
358. K. Gademann, T. Kimmerlin, D. Hoyer and D. Seebach, Peptide folding induces high and selective affinity of a linear and small beta-peptide to the human somatostatin receptor 4, J.Med.Chem., 44, 2460-2468 (2001).
359. R. Hirschmann, W. Q. Yao, M. A. Cascieri, C. D. Strader, L. Maechler, M. A. CichyKnight, J. Hynes, R. D. vanRijn, P. A. Sprengeler and A. B. Smith, Synthesis of potent cyclic hexapeptide NK-1 antagonists. Use of a minilibrary in transforming a peptidal somatostatin receptor ligand into an NK-1 receptor ligand via a polyvalent peptidomimetic, J.Med.Chem., 39, 2441-2448 (1996).
360. D. Giannotti, E. Perrotta, C. Di Bugno, R. Nannicini, N. J. S. Harmat, A. Giolitti, R. Patacchini, A. R. Renzetti, L. Rotondaro, S. Giuliani, M. Altamura and C. A. Maggi, Discovery of potent cyclic pseudopeptide human tachykinin NK-2 receptor antagonists, J.Med.Chem., 43, 4041-4044 (2000).
361. P. Grieco, A. Carotenuto, P. Campiglia, E. Zampelli, R. Patacchini, C. A. Maggi, E. Novellino and P. Rovero, A new, potent urotensin II receptor peptide agonist containing a pen residue at the disulfide bridge, J.Med.Chem., 45, 4391-4394 (2002).
362. P. Grieco, A. Carotenuto, P. Campiglia, L. Marinelli, T. Lama, R. Patacchini, P. Santicioli, C. A. Maggi, P. Rovero and E. Novellino, Urotensin-II receptor ligands. From agonist to antagonist activity, J.Med.Chem., 48, 7290-7297 (2005).
363. S. Foister, L. L. Taylor, J. J. Feng, W. L. Chen, A. Lin, F. C. Cheng, A. B. Smith and R. Hirschmann, Design and synthesis of potent cystine-free cyclic hexapeptide agonists at the human urotensin receptor, Org.Lett., 8, 1799-1802 (2006).
364. A. Carotenuto, P. Griecio, P. Rovero and E. Novellino, Urotensin-II receptor antagonists, Curr.Med.Chem., 13, 267-275 (2006).
365. S. Flohr, M. Kurz, E. Kostenis, A. Brkovich, A. Fournier and T. Klabunde, Identification of nonpeptidic urotensin II receptor antagonists by virtual screening based on a pharmacophore model derived from structure-activity relationships and nuclear magnetic resonance studies on urotensin II, J.Med.Chem., 45, 1799-1805 (2002).
366. F. Lehmann, A. Pettersen, E. A. Currier, V. Sherbukhin, R. Olsson, U. Hacksell and K. Luthman, Novel potent and efficacious nonpeptidic urotensin II receptor agonists, J.Med.Chem., 49, 2232-2240 (2006).
367. D. K. Luci, S. Ghosh, C. E. Smith, J. Qi, Y. Wang, B. Haertlein, T. J. Parry, J. Li, H. R. Almond, L. K. Minor, B. P. Damiano, W. A. Kinney, B. E. Maryano and E. C. Lawson, Phenylpiperidine-benzoxazinones as urotensin-II receptor antagonists: Synthesis, SAR, and in vivo assessment, Bioorg.Med.Chem.Lett., 17, 6489-6492 (2007).
368. P. M. Fischer, Peptide, peptidomimetic, and small-molecule antagonists of the p53-HDM2 protein-protein interaction, Int. J. Pept. Res. Ther., 12, 3-19 (2006).
369. J. K. Murray and S. H. Gellman, Targeting protein-protein interactions: Lessons from p53/MDM2, Biopolymers, 88, 657-686 (2007).
370. A. S. Dudkina and C. W. Lindsley, Small molecule protein-protein inhibitors for the p53-MDM2 interaction, Curr. Top. Med. Chem., 7, 952-960 (2007).
371. C. Garcia-Echeverria, P. Chene, M. J. J. Blommers and P. Furet, Discovery of potent antagonists of the interaction between human double minute 2 and tumor suppressor p53, J. Med. Chem., 43, 3205-3208 (2000).
372. K. Sakurai, C. Schubert and D. Kahne, Crystallographic analysis of an 8-mer p53 peptide analogue complexed with MDM2, J. Am. Chem. Soc., 128, 11000-11001 (2006).
373. J. A. Kritzer, O. M. Stephens, D. A. Guarracino, S. K. Reznik and A. Schepartz, beta-Peptides as inhibitors of protein-protein interactions, Bioorgan. Med. Chem., 13, 11-16 (2005).
374. J. A. Kritzer, M. E. Hodsdon and A. Schepartz, Solution structure of a beta-peptide ligand for hDM2, J. Am. Chem. Soc., 127, 4118-4119 (2005).
375. F. Bernal, A. F. Tyler, S. J. Korsmeyer, L. D. Walensky and G. L. Verdine, Reactivation of the p53 tumor suppressor pathway by a stapled p53 peptide, J. Am. Chem. Soc., 129, 2456 (2007).
376. K. Sakurai, H. S. Chung and D. Kahne, Use of a retroinverso p53 peptide as an inhibitor of MDM2, J. Am. Chem. Soc., 126, 16288-16289 (2004).
377. T. Hara, S. R. Durell, M. C. Myers and D. H. Appella, Probing the structural requirements of peptoids that inhibit HDM2-p53 interactions, J. Am. Chem. Soc., 128, 1995-2004 (2006).
378. R. Fasan, R. L. A. Dias, K. Moehle, O. Zerbe, D. Obrecht, P. R. E. Mittl, M. G. Grutter and J. A. Robinson, Structure-activity studies in a family of betahairpin protein epitope mimetic inhibitors of the p53-HDM2 protein-protein interaction, ChemBioChem, 7, 515-526 (2006).
379. Luke, R. W. A., Jewsbury, P. J. and Cotton, R., WO 2000015657, 2000.
380. R. M. Zhang, T. Mayhood, P. Lipari, Y. L. Wang, J. Durkin, R. Syto, J. Gesell, C. McNemar and W. Windsor, Fluorescence polarization assay and inhibitor design for MDM2/p53 interaction, Anal.Biochem., 331, 138-146 (2004).
381. L. T. Vassilev, B. T. Vu, B. Graves, D. Carvajal, F. Podlaski, Z. Filipovic, N. Kong, U. Kammlott,C. Lukacs, C. Klein, N. Fotouhi and E.A. Liu, In vivo activation of the p53 pathway by small-molecule antagonists ofMDM2, Science, 303, 844-848 (2004).
382. M. D. Cummings, C. Schubert, D. J. Parks, R. R. Calvo, L. V. LaFrance, J. Lattanze, K. L. Milkiewicz and T. B. Lu, Substituted 1,4-benzodiazepine-2,5-diones as alpha-helix mimetic antagonists of the HDM2-p53 protein-protein interaction, Chemical Biology & Drug Design, 67, 201-205 (2006).
383. J. J. Marugan, K. Leonard, P. Raboisson, J. M. Gushue, R. Calvo, H. K. Koblish, J. Lattanze, S. Y. Zhao, M. D. Cummings, M. R. Player, C. Schubert, A. C. Maroney and T. B. Lu, Enantiomerically pure 1,4-benzodiazepine-2,5-diones as Hdm2 antagonists, Bioorg.Med.Chem.Lett., 16, 3115-3120 (2006).
384. K. Ding, Y. Lu, Z. Nikolovska-Coleska, S. Qiu, Y. S. Ding, W. Gao, J. Stuckey, K. Krajewski, P. P. Roller, Y. Tomita, D. A. Parrish, J. R. Deschamps and S. M. Wang, Structure-based design of potent non-peptide MDM2 inhibitors, J.Am.Chem.Soc., 127, 10130-10131 (2005).
385. K. Ding, Y. P. Lu, Z. Nikolovska-Coleska, G. P. Wang, S. Qiu, S. Shangary, W. Gao, D. G. Qin, J. Stuckey, K. Krajewski, P. P. Roller and S. M. Wang, Structure-based design of spiro-oxindoles as potent, specific small-molecule inhibitors of the MDM2-p53 interaction, J.Med.Chem., 49, 3432-3435 (2006).
386. A. L. Bowman, Z. Nikolovska-Coleska, H. Z. Zhong, S. M.Wang and H.A. Carlson, Small molecule inhibitors of the MDM2-p53 interaction discovered by ensemblebased receptor models, J. Am. Chem. Soc., 129, 12809-12814 (2007).
387. Y. P. Lu, Z. Nikolovska-Coleska, X. L. Fang, W. Gao, S. Shangary, S. Qiu, D. G. Qin and S. M. Wang, Discovery of a nanomolar inhibitor of the human murine double minute 2 (MDM2)-p53 interaction through an integrated, virtual database screening strategy, J.Med.Chem., 49, 3759-3762 (2006).
388. F. Lu, S. W. Chi, D. H. Kim, K. H. Han, I. D. Kuntz and R. K. Guy, Proteomimetic libraries: Design, synthesis, and evaluation of p53-MDM2 interaction inhibitors, J.Comb.Chem., 8, 315-325 (2006).