Tethered libraries: Solid-phase synthesis of substituted urea-linked bicyclic guanidines

Journal of Combinatorial Chemistry

Volumn 3, Issue 2, 2001, Pages 189-195

  Acharya, Achyuta N ^a   Nefzi, Adel ^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

BICYCLO COMPOUND; GUANIDINE DERIVATIVE; UREA;

ARTICLE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

BICYCLO COMPOUNDS; COMBINATORIAL CHEMISTRY TECHNIQUES; GUANIDINES; UREA;

EID: 0035291374     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc0000803     Document Type: Article

References (34)

1. (a) Gallop, M. A.; Barret, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. Applications of Combinatorial Technologies to Drug Discovery. Part 1. Background and Peptide Combinatorial Libraries. J. Med. Chem. 1994, 37, 1233-1251.
2. (b) 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.
3. (c) Thompson, L. A.; Ellman, J. A. Synthesis and Applications of Small Molecule Libraries. Chem. Rev. 1996, 96, 555-600.
4. (d) Fruchtel, J. S.; Jung, G. Organic Chemistry on Solid Supports. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42.
5. (e) Balkenhohl, F.; Bussche-Hunnefeld, C. von dem: Lansky, A.; Zechel, C. Combinatorial Synthesis of Small Organic Molecules. Angew Chem., Int. Ed. Engl. 1996, 35, 2288-2337.
6. (f) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Solid-Phase Organic Reactions: A Review of the Recent Literature. Tetrahedron 1996, 52, 4527-4554.
7. (g) Nefzi, A.; Ostresh, J. M.; Houghten, R. A. The Current Status of Heterocyclic Combinatorial Libraries. Chem. Rev. 1997, 97, 449-472.
8. 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.
9. Ganellin, C. R. In Chron. Drug Discovery; Bindra, J. S., Lednicer, D., Eds.; Wiley: New York, 1982; Vol. 1 pp 1-38.
10. Katsura, Y.; Tomishi, T.; Inoue, Y.; Sakane, K.; Matsumoto, Y.; Morinaga, C.; Ishikawa, H.; Takasugi, H. Anti-Helicobacter pylori Agents. 4. 2-(Substituted guanidino)-4-phenylthiazoles and Some Structurally Rigid Derivatives. J. Med. Chem. 2000, 43, 3315-3321.
11. Gilman, A. G.; Goodman, L. S.; Goodman, A. The Pharmacological Basis of Therapeutics, 6th ed.; Macmillan Publishing Co.: New York, 1980; p 380.
12. Smetes, L. A.; et al. Antitumor Agent-m-Iodobenzylguanidine. Cancer Chemother. Pharmacol. 1988, 21, 9-24.
13. Greenhill, J. L.; Lue, P. In Progress in Medicinal Chemistry; Ellis, G. P., Luscombe, D. K., Eds.; Elsevier Science: New York, 1993; Vol. 30, Chapter 5.
14. 2 Receptor Agonist. J. Med. Chem. 1985, 28, 1414-1422.
15. Corelli, F.; Dei, D.; Monoche, G. D.; Botta, B.; Delucca, C.; Carmiganni, M.; Volpe, A. R.; Botta, M. Hypotensive-Caracasanamide. Bioorg Med. Chem. Lett. 1996, 6, 653-658.
16. Ohnota, H.; Koizumi, T.; Tsutsumi, N.; Kobayashi, M.; Inoue, S.; Sato, F. Insulin Secretagouge-Potassium/ATP Channel Opener-BTS 67,582. J. Pharmocol. Exp. Ther. 1994, 269, 489.
17. + Channels. J. Med. Chem. 1998, 41, 3048-3061.
18. Reddy, N. L.; Cannaughton, S.; Daly, D.; Fischer, J. B.; Goldin, S. M.; Hu, L. H.; Subbarao, K.; Durant, G. J. Synthesis and Characterization of N-(acenaphthyl-4-yl)-N′-(4-methoxynaphth-1-yl)guanidine as a Glutamate Release Inhibitor and Potential Anti-ischemic Agent. Bioorg. Med. Chem. Lett. 1995, 5, 2259-2262.
19. Hu, L. Y.; Durant, G.; Guo, J. Q.; Maillard, M.; Wolcott, T.; Berlove, D. Synthesis and Structure-Activity Relationships of Substituted N-aryl-N-aralkylguanidines as Anti-seizure Agents. Abstracts of Papers, 214th National Meeting of the American Chemical Society, Las Vegas, NV, 1997; American Chemical Society: Washington, DC. 1997; MEDI 32.
20. Jhadav, P. K.; Woerner, F. J.; Lam, P. Y. S.; Hodge, C. N.; Eyermann, C. J.; Man, H. W.; Daneker, W. F.; Bacheler, L. T.; Rayner, M. M.; Meek, J. L.; Erickson-Viitanen, S.; Jackson, D. A.; Calabrese, J. C.; Schadt, M.; Chang, C. H.; Nonpeptide Cyclic Cyanoguanidines as HIV-1 Protease Inhibitors: Synthesis, Structure-Activity Relationships, and X-ray Crystal Structure Studies. J. Med. Chem. 1998, 41. 1446-1455.
21. Ostresh, J. M.; Schoner, C. C.; Hamshin, V. T.; Nefzi, A.; Meyer, J.-P.; Houghten, R. A. Solid-Phase Synthesis of Trisubstituted Bicyclic Guanidines via Cyclization of Reduced N-Acylated Dipeptides. J. Org. Chem. 1998, 63, 8622-8623.
22. Blondelle, S. E.; Crooks, E.; Ostresh, J. M.; Houghten, R. A. Mixture-Based Heterocyclic Combinatorial Positional Scanning Libraries: Discovery of Bicyclic Guanidines having Potent Antifungal Activities Against Candida albicans and Cryptococcus neoformans. Antimicrob. Agents. Chemother. 1999, 43, 106-114.
23. The MDDR database contains more than 6000 compounds having an urea scaffold.
24. Amagase, K.; Ikeda, K.; Okabe, S. Antisecretory and Ulcer Healing Effects of S-0509, A Novel CCK/gastrin Receptor Antagonist, in Rats. Dig. Dis. Sci. 1999, 44, 879-888.
25. Nakao, K.; Shimizu, R.; Hitoshi, K.; Yasuhara, M.; Hashimura, Y.; Suzuki, T.; Fujita, T.; Ohmizu, H. Quantitative Structure-Activity Analyses of Novel Hydroxyphenylurea Derivatives as Antioxidants. Bioorg. Med. Chem. 1998, 6, 849-868.
26. Tanaka, A.; Terasawa, T.; Hagihara, H.; Sakuma, Y.; Ishibe, N.; Sawada, M.; Takasugi, H.; Tanaka, H. Inhibitors of Acyl-CoA:Cholesterol O-acyltransferase (ACAT). Part 1: Identification and Structure-Activity Relationships of a Novel Series of Substituted N-alkyl-N-biphenylylmethyl-N′-arylureas. Bioorg. Med. Chem. 1998, 6, 15-30.
27. Jacobsen, E. J.; Mitchell, M. A.; Hendges, S. K.; Belonga, K. L.; Skaletzky, L. L.; Stelzer, L. S.; Lindberg, T. J.; Fritzen, E. L.; Schostarez, H. J.; O'Sullivan, T. J., Maggiora, L. L.; Stuchly, C. W.; Laborde, A. L.; Kubicek, M. F.; Poorman. R. A.; Beck, J. M.; Miller, H. R.; Petzold, G. L.; Scott, P. S.; Truesdell, S. E.; Wallace, T. L.; Wilks, J. W.; Fisher, C.; Goodman, L. V.; Kaytes, P. S.; Ledbetter, S. R.; Powers, E. A.; Vogeli, G.; Mott, J. E.; Trepod, C. M.; Staples, D. J.; Baldwin, E. T.; Finzel, B. C. Synthesis of a Series of Stromelysin-Selective Thiazole Urea Matrix Metalloproteinase Inhibitors. J. Med. Chem. 1999, 42, 1525-1536.
28. Ostresh, J. M.; Husar, G. M.; Blondelle, S. E.; Dorner, 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.
29. Cuervo, J. H.; Weitl, F.; Ostresh, J. M.; Hamshin, V. T.; Hannah, A. L.; Houghten, R. A. Polyalkylamine Chemical Combinatorial Libraries. In Peptides 94: Proceedings of the 23rd European Peptide Symposium; Maia, H. L. S., Ed.; ESCOM: Leiden, The Netherlands, 1995; pp 465-466.
30. Nefzi, A.; Dooley, C.; Ostresh, J. M.; Houghten, R. A. Combinatorial Chemistry: From Peptides and Peptidomimetics to Small Organic and Heterocyclic Compounds. Bioorg. Med. Chem. Lett. 1998, 8, 2273-2278.
31. Pinilla, C.; Appel, J. R.; Blanc, P.; Houghten, R. A.; Rapid Identification of High Affinity Peptide Ligands Using Positional Scanning Synthetic Peptide Combinatorial Libraries. Biotechniques 1992, 13, 901-905.
32. 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.
33. Kaiser, E. T.; Colescott, R. L.; Bossinger, 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.
34. Houghten, R. A.; Bray, M. K.; DeGraw, S. T.; Kirby, C. J. Simplified Procedure for Carrying Out Simultaneous Multiple Hydrogen Fluoride Cleavage of Protected Peptide Resins. Int. J. Pept. Protein Res. 1986, 27, 6763-6768.