Novel approaches for the solid-phase synthesis of biheterocyclic dihydroimidazole analogues

Journal of Combinatorial Chemistry

Volumn 4, Issue 3, 2002, Pages 214-222

  Acharya, Achyuta N ^a   Ostresh, John M ^a   Houghten, Richard A ^a  

^a TORREY PINES INSTITUTE FOR MOLECULAR STUDIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; BENZIMIDAZOLE DERIVATIVE; FUSED HETEROCYCLIC RINGS; IMIDAZOLE DERIVATIVE; RESIN;

AMINATION; ARTICLE; CHEMISTRY; COMBINATORIAL CHEMISTRY; DRUG DESIGN; METHODOLOGY; SYNTHESIS;

AMINATION; AMINO ACIDS; BENZIMIDAZOLES; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG DESIGN; HETEROCYCLIC COMPOUNDS, 2-RING; IMIDAZOLES; RESINS, SYNTHETIC;

EID: 0039889657     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc010067y     Document Type: Article

References (48)

1. (a) Houghten, R. A.; Pinilla, C.; Appel, J. R.; Blondelle, S. E.; Dooley, C. T.; Eichler, J.; Nefzi, A.; Ostresh, J. M. Mixture-Based Synthetic Combinatorial Libraries. J. Med. Chem. 1999, 42, 3743-3778.
2. (b) Franzen, R. G. Recent Advances in the Preparation of Heterocycles on Solid Support: A Review of the Literature. J. Comb. Chem. 2000, 2, 195-214.
3. (c) Nefzi, A.; Ostresh, J. M.; Houghten, R. A. The Current Status of Heterocyclic Combinatorial Libraries. Chem. Rev. 1997, 97, 449-472.
4. (d) Thompson, L. A.; Ellman, J. A. Synthesis and Application of Small Molecule Libraries. Chem. Rev. 1996, 96, 555-600.
5. (e) Gordon, E. M.; Barret, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. Applications of Combinatorial Technologies to Drug Discovery. 2. Combinatorial Organic Synthesis, Library Screening Strategies, and Future Directions. J. Med. Chem. 1994, 37, 1385-1401.
6. Roth, T.; Morningstar, M. L.; Boyer, P. L.; Hughes, S. H.; Buckheit, R. W., Jr.; Michejda, C. J. Synthesis and Biological Activity of Novel Nonnucleoside Inhibitors of HIV-1 Reverse Transcriptase. 2-Aryl-Substituted Benzimidazoles. J. Med. Chem. 1997, 40, 4199-4207.
7. Kim, J. S.; Gatto, B.; Yu, C.; Liu, A.; Liu, L. F.; LaVoie, E. J. Substituted 2,5′-Bi-1H-Benzimidazoles: Topoisomerase I Inhibition and Cytotoxicity. J. Med. Chem. 1996, 39, 992-995.
8. Porcari, A. R.; Devivar, R. V.; Kucera, L. S.; Drach, J. C.; Townsend, L. B. Design, Synthesis, and Antiviral Evaluations of 1-(Substituted benzyl)-2-substituted-5,6-dichlorobenzimidazoles as Nonnucleoside Analogues of 2,5,6-Trichloro-1-(β-ribofuranosyl)benzimidazole. J. Med. Chem. 1998, 41, 1252-1262.
9. Zarrinmayeh, H.; Nunes, A. M.; Ornstein, P. L. Z. D. M.; Arnold, M. B.; Schober, D. A.; Gackenheimer, S. L. B. R. F.; Hipskind, P. A.; Britton, T. C.; Cantrell, B. E.; Gehlert, D. R. Synthesis and Evaluation of a Series of Novel 2-[(4-Chlorophenoxy)methyl]-benzimidazoles as Selective Neuropeptide Y Y1 Receptor Antagonists. J. Med. Chem. 1998, 41, 2709-2719.
10. Kohara, Y.; Kubo, K.; Imamiya, E.; Wada, T.; Inada, Y.; Naka, T. Synthesis and Angiotensin II Receptor Antagonistic Activities of Benzimidazole Derivatives Bearing Acidic Heterocycles as Novel Tetrazole Bioisosteres. J. Med. Chem. 1996, 39, 5228-5235.
11. Lombardy, R. L.; Tanious, F. A.; Ramachandran, K.; Tidwell, R. R.; Wilson, W. D. Synthesis and DNA Interactions of Benzimidazole Dications Which Have Activity against Opportunistic Infections. J. Med. Chem. 1996, 39, 1452-1462.
12. Gua, Z.; Zhou, D.; Schultz, P. G. Designing Small-Molecule Switches for Protein-Protein Interactions. Science 2000, 288, 2042-2045.
13. Artico, M.; Silvestri, R.; Pagnozzi, E.; Bruno, B.; Novellino, E.; Greco, G.; Massa, S.; Ettorre, A.; Loi, A. G.; Scintu, F.; Colla, P. L. Structre-Based Design, Synthesis, and Biological Evaluation of Novel Pyrrolyl Aryl Sulfones: HIV-1 NonNucleoside Reverse Transcriptase Inhibitors Active at Nanomolar Concentrations. J. Med. Chem. 2000, 43, 1886-1891.
14. Talley, J. J.; Bertenshaw, S. R.; Brown, D. L.; Carter, J. S.; Graneto, M.; M. J.; Kellog, M. S.; Koboldt, C. M.; Yuan, J.; Zhang, Y. Y.; Seibert, K. N-[[(5-Methyl-3-phenylisozol-4-yl)-phenyl]sulfonyl]propanamide: A Potent and Selective Inhibitor of COX-2 for Parenteral Administation. J. Med. Chem. 2000, 43, 1661-1663.
15. Scozzafava, A.; Supuran, C. T. Protease Inhibitors: Synthesis of Potent Bacterial Collagenase and Matrix Metalloproteinase Inhibitors Incorporating N-4-Nitrobenzylsulfonylglycine Hydroxamate Moieties. J. Med. Chem. 2000, 43, 1858-1865.
16. Schelkum, R. M.; Yuen, P.-W.; Serpa, K.; Meltzer, L. T.; Wise, L. D.; Whittemore, E. R.; Woodward, R. M. Subtype-Selective N-Methyl-D-aspartate Receptor Antagonists: Benzimidazolone and Hydantoin as Phenol Replacements. J. Med. Chem. 2000, 43, 1892-1897.
17. Coffey, D. S.; McDonald, A. I.; Overman, L. E.; Rabinowitz, M. H.; Renhowe, P. A. A Practical Entry to the Crambescidin Family of Guanidine Alkaloids. Enantioselective Total Syntheses of Ptilomycalin A, Crambescidin 657 and Its Methyl Ester (Neofolitispates 2), and Crambescidin 800. J. Am. Chem. Soc. 2000, 122, 4893-4903.
18. Ohtani, I.; Kusumi, T.; Kakisawa, H.; Kashman, Y.; Hirsh, S. Structure and Chemical Properties of Ptilomycalin A. J. Am. Chem. Soc. 1992, 114, 8472-8479.
19. Jares, E. A.-E.; Sakai, R.; Rinehart, K. L. Crambescidins: New Antiviral and Cytotoxic Compounds from the Sponge Crambe crambe. J. Org. Chem. 1991, 56, 5712-5715.
20. Kashman, Y.; Hirsh, S.; McConnell, O. J.; Ohtani, I.; Kusumi, T.; Kakisawa, H. Ptilomycalin A: A Novel Polycyclic Guanidine Alkaloid of Marine Origin. J. Am. Chem. Soc. 1989, 111, 8925-8926.
21. Ohtani, I. I.; Kusumi, T.; Kakisawa, H. An Insight into the Conformation of Ptilomycalin A. The NMR Properties of Trifluoroacetylated Spermidine Analogues. Tetrahedron Lett. 1992, 33, 2525-2528.
22. 2+-ATPase Inhibitor, Competitively Interacts with ATP at Its Binding Site. Eur. J. Pharmacol. 1996, 310, 95-98.
23. + Channels. J. Med. Chem. 1998, 41, 3048-3061.
24. Ganelin, C. R. In Chronicles of Drug Discovery; Bindra, J. S., Lednicer, D., Eds.; Wiley: New York, 1982; Vol. 1, pp 1-38.
25. th ed.; Macmillan Publishing Co.: New York, 2001; Chapter 10, pp 215-258.
26. (b) Greenhill, J. V.; Lue, P. Prog. Med. Chem. 1993, 30, 203.
27. Matsumoto, H.; Ikeda, K.; Nagata, N.; Takayanagi, H.; Mizuno, Y.; Tanaka, M.; Sasaki, T. Synthesis of 2,8-Disubstituted Imidazo[1,5-a]pyrimidines with Potent Anti-tumor Activity. J. Med. Chem. 1999, 42, 1661-1666.
28. Bihan, G. L.; Rondu, F.; Pele, A.-T.; Wang, X.; Lidy, S.; Touboul, E.; Lamouri, A.; Dive, G.; Huet, J.; Pfeiffer, B.; Renard, P.; Guardiola, B.-L.; Manechez, D.; Penicaud, L.; Ktorza, A.; Godfroid, J.-J. Design and Synthesis of Imidazoline Derivatives Active on Glucose Homeostasis in a Rat Model of Type II Diabetes. 2. Syntheses and Biological Activities of 1,4-Dialkyl-, 1,4-Dibenzyl, and 1-Benzyl-4-alkyl-2-(4′,5′-dihydro-1′H-imidazol-2′yl) piperazines and Isosteric Analogues of Imidazoline. J. Med. Chem. 1999, 42, 1587-1603.
29. Kawamoto, H.; Ozaki, S.; Itoh, Y.; Miyaji, M.; Arai, S.; Nakashima, H.; Kato, T.; Ohta, H.; Iwasawa, Y. Discovery of the First Potent and Selective Small Molecule Opioid-Receptor-like (ORL1) Antagonist: 1-[(3R,4R-1-Cyclooctyl-methyl-3-hydroxymethyl-4-piperidyl]-3-ethyl-1,3- dihydro2H-benzimidazol-2-one (J-113397). J. Med. Chem. 1999, 42, 5061-5063.
30. Lee, J.; Murray, W. V.; Rivero, R. A. Solid Phase Synthesis of 3,4-Disubstituted-7-carbonyl-1,2,3,4-tetrahydroquinoxalin-2-ones. J. Org. Chem. 1997, 62, 3874-3879.
31. Morales, G. A.; Corbett, J. W.; DeGrado, W. F. Solid-Phase Synthesis of Benzopiperazinones. J. Org. Chem. 1998, 63, 1172-1177.
32. Schwarz, M. K.; Tumelty, D.; Gallop, M. A. Solid-Phase Synthesis of 1,5-Benzodiazepine-2-ones. Tetrahedron Lett. 1998, 39, 8397-8400.
33. Schwarz, M. K.; Tumelty, D. G. M. A. Solid-Phase Synthesis of 3,5-Disubstituted 2,3-Dihydro-1,5-benzothiazepin-4(5H)-ones. J. Org. Chem. 1999, 64, 2219-2231.
34. Ostresh, J. M.; Schoner, C. C.; Hamashin, V. T.; Nefzi, A.; Meyer, J.-P.; Houghten, R. A. Solid Phase Synthesis of Trisubstituted Bicyclic Guanidines via Cyclicization of Reduced N-Acylated Dipeptides. J. Org. Chem. 1998, 63, 8622-8623.
35. (a) Fodor, G.; Nagubandi, S. Correlation of the Von Braun, Ritter, Bischler-Napieralski, Beckmann and Schmidt Reactions via Nitrilium Salt Intermediates. Tetrahedron 1980, 36, 1279-1300.
36. (b) Gauthier, J. A.; Jirkovsky, I. U.S. Patent 4379926, 1983.
37. 4). Tetrahedron Lett. 2000, 41, 6531-6535.
38. Yeh, C. M.; Tung, C. L.; Sun, C.-M. Combinatorial Liquid-Phase Synthesis of Structurally Diverse Benzimidazole Libraries. J. Comb. Chem. 2000, 2, 341-348.
39. (a) Acharya, A. N.; Ostresh, J. M.; Houghten, R. A. Solid-Phase Synthesis of Substituted Imidazoline-Tethered 2,3-Diketopiperazines, Cyclic Ureas, and Cyclic Thioureas. J. Comb. Chem. 2001, 3, 612-623.
40. (b) Acharya, A. N.; Ostresh, J. M.; Houghten, R. A. A Novel Approach for Solid-Phase Synthesis of Substituted Imidazolines and Bis-Imidazolines. J. Org. Chem. 2001, 66, 8673-8676.
41. Eichler, J.; Houghten, R. A. Synthesis of Cyclic Disulfide Peptides-Comparison of Oxidation Methods. Protein Pept. Lett. 1997, 4, 157-164.
42. Acharya, A. N.; Ostresh, J. M.; Houghten, R. A. A Novel Approach for the Solid-Phase Synthesis of Substituted Cyclic Guanidines, Their Respective Bis Analogues, and N-Acylated Guanidines from N-Acylated Amino Acid Amides. J. Comb. Chem. 2001, 3, 578-589.
43. Echavarren, A.; Gala, A.; Lehn, J.-M.; Mendoza, J. Chiral Recognition of Aromatic Carboxylate Anions by an Optically Active Abiotic Receptor Containing a Rigid Guanidinium Binding Subunit. J. Am. Chem. Soc. 1989, 111, 4994-4995
44. Acharya, A. N.; Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Tethered Libraries: Solid-Phase Synthesis of Substituted Urea-Linked Bicyclic Guanidines. J. Comb. Chem. 2001, 3, 189-195.
45. Ostresh, J. M.; Husar, G. M.; Blondelle, S. E.; Dörner, B.; Weber, P. A.; Houghten, R. A. "Libraries from libraries": Chemical Transformation of Combinatorial Libraries To Extend the Range and Repertoire of Chemical Diversity. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 11138-11142
46. Houghten, R. A. General Method for the Rapid Solid-Phase Synthesis of Large Numbers of Peptides: Specificity of Antigen-Antibody Interaction at the Level of Individual Amino Acids. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 5131-5135.
47. Kaiser, E. T.; Colescott, R. L.; Blossinger, C. D.; Cook, P. I. Color Test for Detection of Free Terminal Amino Groups in the Solid-Phase Synthesis of Peptides. Anal. Biochem. 1970, 34, 595-598.
48. Houghten, R. A.; Bray, M. K.; DeGraw, S. T.; Kirby, C. J. Simplified Procedure for Carrying Out Simultaneous Multiple Hydrogen Fluoride Cleavages of Protected Peptide Resins. Int. J. Pept. Protein Res. 1986, 27, 673-678