Coiiformatioiially homogeneous heterocyclic pseudotetrapeptides as three-dimensional scaffolds for rational drug design: ReceptorSelective somatostatin analogues

Angewandte Chemie - International Edition

Volumn 48, Issue 26, 2009, Pages 4725-4729

  Beierle, John M ^a   Horne, W Seth ^a   Van Maarseveen, Jan H ^a   Waser, Beatrice ^b   Reubi, Jean Claude ^b   Ghadiri, M Reza ^a,c  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF BERN   (Switzerland)

^c UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

Conformation analysis; Cyclic peptides; Drug design; Structure activity relationships; Trlazoles

Indexed keywords

CONFORMATION ANALYSIS; CYCLIC PEPTIDES; DRUG DESIGN; STRUCTURE-ACTIVITY RELATIONSHIPS; TRLAZOLES;

AMIDES; AMINES; SCAFFOLDS; STRUCTURAL ANALYSIS;

PEPTIDES;

DRUG DERIVATIVE; HETEROCYCLIC COMPOUND; ISOPROTEIN; OLIGOPEPTIDE; SOMATOSTATIN; SOMATOSTATIN RECEPTOR;

ARTICLE; CHEMISTRY; CONFORMATION; DRUG DESIGN; HUMAN; METABOLISM; PROTEIN BINDING; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; HETEROCYCLIC COMPOUNDS; HUMANS; MOLECULAR CONFORMATION; OLIGOPEPTIDES; PROTEIN BINDING; PROTEIN ISOFORMS; RECEPTORS, SOMATOSTATIN; SOMATOSTATIN; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 66749190071     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200805901     Document Type: Article

References (62)

1. For selected reviews, see: a) S. Reissmann, D. Imhof, Curr. Med. Chem. 2004, 11, 2823;
2. b) P. Li, P.P. Roller, J. Xu, Curr. Org. Chem. 2002, 6,411;
3. c) M. MacDonald, J. Aube, Curr. Org. Chem. 2001, 5, 417;
4. d) H. Kessler, R. Gratias, G. Hessler, M. Gurrath, G. Mueller, Pure AppL Chem. 1996, 68,1201;
5. e) H. Kessler, Angew. Chem. 1982, 94,703;
6. Angew. Chem. Int. Ed. Engl. 1982, 21, 512.
7. a) R. E. Shute, M. Kawai, D. H. Rich, Tetrahedron 1988, 44, 685;
8. b) M. Kawai, D. H. Rich, Tetrahedron Lett. 1983, 24, 5309.
9. M. Kawai, R. D. Jasensky, D. H. Rich, J. Am. Chem. Soc 1983, 705, 4456.
10. a) H. Tamamura, et al., J. Med. Chem. 2005, 48, 3280;
11. b)N. Loiseau, J.-M. Gomis, J. Santolini, M. Delaforge, F. Andre, Biopolymers 2003, 69, 363;
12. c) W. D. F. Meutermans, G. T. Bourne, S.W. Golding, D. A. Horton, M. R. Campitelli, D. Craik, M. Scanlon, M. L. Smythe, Org. Lett. 2003, 5, 2711;
13. d) D. A. Horton, G. T. Bourne, M. L. Smythe, Mol., Diversity 2002, 5, 289;
14. e) Y. Terada, M. Kawai, D.H. Rich, Int. J. Pept. Protein Res. 1989, 33, 3;
15. f) M. Kawai, R. S. Pottorf, D. H. Rich, J. Med. Chem. 1986, 29, 2409.
16. M. P. Glenn, M. J. Kelso, J. D. A. Tyndall, D. P. Fairlie, J. Am. Chem. Soc 2003, 725, 640.
17. a) A. Montero, J. M. Beierle, C. A. Olsen, M. R. Ghadiri, J. Am. Chem. Soc. 2009, 131, 3033;
18. b) D. Seebach, et al., HeIv. Chim. Acta 2008, 91,1736;
19. c) A. S. Norgren, F. Buettner, S. Prabpai, P. Kongsaeree, P. I. Arvidsson, J. Org. Chem. 2006, 71, 6814;
20. d) F. Schumann, A. Mueller, M, Koksch, G. Mueller, N. Sewald, J. Am. Chem. Soc. 2000, 122,12009.
21. V. D. Bock, R. Perciaccante, T. P. Jansen, H. Hiemstra, J. H. van Maarseveen, Org. Lett. 2006, 8, 919.
22. a) W. S. Home, C. A. Olsen, J. M. Beierle, A. Montero, M. R. Ghadiri, Angew. Chem. 2009,121,4812;
23. Angew. Chem. Int. Ed. 2009, 48, 4718;
24. b) Y. Chen, M. Lopez-Sanchez, D. N. Savoy, D. D. Billadeau, G. S. Dow, A. P. Kozikowski, J. Med. Chem. 2008, 51, 3437;
25. c) V. D. Bock, D. Speijer, H. Hiemstra, J. H. van Maarseveen, Org. Biomol Chem. 2007, 5, 971;
26. d) R. A. Turner, A. G. Oliver, R. S. Lokey, Org. Lett. 2007, 9, 5011;
27. e) G. Appendino, S. Bacchiega, A. Minassi, M. Grazia Caseio, L. De Petrocellis, V. Di Marzo, Angew. Chem. 2007, 119, 9472;
28. Angew. Chem. Int. Ed. 2007,46,9312;
29. f) Y. L. Angell, K. Burgess, Chem. Soc. Rev. 2007, 36,1674;
30. g) W. J. Choi, Z.-D. Shi, K. M. Worthy, L. Bindu, R. G. Karki, M. C Nicklaus, R. J. Fisher, T. R. Burke, Bioorg. Med. Chem. Lett. 2006, 16, 5265;
31. h) N. G. Angelo, P. S. Arora, J. Am. Chem. Soc. 2005, 127, 17134;
32. i) A. Brik, J. Alexandratos, Y.-C. Lin, J. H. Elder, A. J. Oison, A. Wlodawer, D. S. Goodsell, C.-H. Wong, ChemBioChem 2005, 6,1167;
33. j) Y. Angell, K. Burgess, J. Org. Chem. 2005, 70, 9595.
34. a) J. H. van Maarseveen, W. S. Home, M. R. Ghadiri, Org. Lett. 2005, 7, 4503;
35. b) W. S. Home, M. K. Yadav, C. D. Stout, M. R. Ghadiri, J. Am. Chem. Soc. 2004, 726, 15366;
36. c) W. S. Home, C. D. Stout, M. R. Ghadiri, J. Am. Chem. Soc. 2003, 125, 9372.
37. Trisubstituted 1,2,3-triazoles have been employed as amidebond surrogates in ghrelin mimics:
38. a) A. Moulin, L. Demange, J. Ryan, C. M'Kadmi, X.-C. Galleyrand, X Martinez, X.-A. Fehrentz, Bioorg. Med. Chem. Lett. 2008, 18, 164;
39. b) A. Moulin, et al., J. Med. Chem. 2008, 57, 689;
40. c) A. Moulin, et al., J. Med. Chem. 2007, 50, 5790.
41. For a discussion of conformational homogeneity, see: J. Chatterjee, D. Mierke, H. Kessler, J. Am. Chem. Soc 2006, 128, 15164.
42. a) G. V. Nikiforovich, G. R. Marshall, S. Achilefu, Chem. Biol. Drug Des. 2007, 69, 163;
43. b) C. R. R. Grace, L. Durrer, S.C. Koerber, J. Erchegyi, J. C Reubi, J. E. Rivier, R. Riek, J. Med. Chem. 2005, 48, 523;
44. c) C. R. R. Grace, S.C. Koerber, J. Erchegyi, J. C. Reubi, J. Rivier, R. Riek, J. Med. Chem. 2003, 46, 5606;
45. d) G. Weckbecker, I. Lewis, R. Albert, H. Schmid, D. Hoyer, C. Bruns, Nat. Rev. Drug Discovery 2003, 2, 999;
46. e) R. Hirschmann, et al., J. Med Chem. 1998, 41, 1382;
47. f) R.-H. Mattern, T.-A. Tran, M. Goodman, J. Med. Chem. 1998, 41, 2686;
48. g) S. P. Rohrer, et al., Science 1998, 282, 737;
49. h) G. Melacini, Q. Zhu, G. Osapay, M. Goodman, J. Med. Chem 1997, 40, 2252;
50. i) G. Melacini, Q. Zhu, M. Goodman, Biochemistry 1997, 36, 1233;
51. j) H. Kessler, J. W. Bats, C. Griesinger, S. KoIl, M. Will, K. Wagner, J. Am. Chem. Soc. 1988, 110,1033 ;
52. k) C. Gilon, et al., J. Med. Chem. 1998, 41, 919;
53. H. Kessler, M. Bernd, I. Damm, Tetrahedron Lett. 1982, 23, 4685;
54. m) D. F. Veber, et al., Nature 1981,292,55;
55. n) E. Graf von Roedern, E. Lohof, G. Hessler, M. Hoffmann, H. Kessler, J. Am. Chem. Soc. 1996, 115,10156.
56. T. R. Chan, R. Hilgraf, K. B. Sharpless, V. V. Fokin, Org. Lett. 2004, 6, 2853.
57. S. Punna, J. Kuzelka, Q. Wang, M. G. Finn, Angew. Chem. 2005, 117, 2255;
58. Angew. Chem. Int. Ed. 2005, 44, 2215.
59. A. T. Brilnger, et al., Acta Crystallogr. Sect. D 1998, 54, 905.
60. a) Y. Fukunishi, S. Kubota, C. Kanai, H. Nakamura, J. ComputAided MoL Des. 2006, 20, 237;
61. b) R. L. DesJarlais, G. L. Seibel, I. D. Kuntz, P. S. Fürth, J. C. Alvarez, P. R. Ortiz de Montellano, D. L. DeCamp, L. M. Babe, C. S. Craik, Proc. Natl. Acad Sci. USA 1990, 87, 6644.
62. J. C. Reubi, J. C. Schaer, B. Waser, S. Wenger, A. Heepler, J. Schmitt, H. R. Mäcke, Eur. J. Nuclear Med. 2000, 27, 273.