Synthesis of 7-membered cyclic hydroxyguanidines: Novel HIV-1 protease inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 17, 1997, Pages 2145-2148

  Jadhav, Prabhakar K ^a   Woerner, Francis J ^a   Man, Hon Wah ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PROTEINASE INHIBITOR;

ARTICLE; DRUG SYNTHESIS; ENZYME BINDING; ENZYME INHIBITION; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 0030924505     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00121-2     Document Type: Article

References (20)

1. West, M. L.; Fairlie, D. P. Trends Pharmacol Sciences 1995, 16, 67.
2. Blundell, T. L. Trends Biochem. Sci. 1990, 15, 425.
3. Darke, P. L.; Huff, J. R. Adv. Pharm. 1994, 25, 399.
4. Tomasselli, A. G. Chim. Oggi. 1992, 9, 6.
5. Moyle, G.; Gazzard, B. Drugs 1996, 57, 701.
6. Wlodawer, A.; Erickson, J. W. Annu. Rev. Biochem. 1993, 62, 543.
7. (a) Lam, P. Y. S.; Jadhav, P. K.; Eyermann, C. J.; Hodge, C. N.; Ru, Y.; Bacheler, L. T.; Meek, J. L.; Otto, M. J.; Rayner, M. M.; Wong, Y. N.; Chang, C.-H.; Weber, P. C.; Jackson, D. A.; Sharpe, T. R.; Erickson-Viitanen, S. Science 1994, 263, 380.
8. (b) Nugiel, D. A.; Jacobs, K.; Worley, T.; Patel, M.; Kaltenbach III, R. F.; Meyer, D. T.; Jadhav, P. K.; Delucca, G. V.; Smyser, T. E.; Klabe, R. M.; Bacheler, L. T.; Rayner, M. M.; Seitz, S. P. J. Med. Chem. 1996, 39, 2156.
9. (c) Lam, P. Y. S.; Ru, Y.; Jadhav, P. K.; Aldrich, P. E.; Delucca, G. V.; Eyermann, C. J.; Chang, C.-H.; Emmett, G.; Holler, E. R.; Daneker, W. F.; Li, L.; Confalone, P. N.; McHugh, R. J.; Han, Q.; Markwalder, J. A.; Seitz, S. P.; Bacheler, L. T.; Rayner, M. M.; Klabe, R. M.; Shum, L.; Winslow, D. L.; Kornhauser, D. M.; Jackson, D. A.; Erickson-Viitanen, S.; Sharp, T. R.; Hodge, C. N. J. Med. Chem. 1996, 39, 3514.
10. (a) Cyclic oxamide: Jadhav, P. K.; Man, H. W. Tetrahedron Letts. 1996, 37, 1153.
11. (b) Cyclic sulfamide: Jadhav, P. K.; Woerner, F. J. Tetrahedron Letts. 1995, 36, 6383.
12. (c) cyclic cyanoguandine: Jadhav, P. K.; Woerner, F. J.; Lam, P. Y. S.; Hodge, C. N.; Eyermann, C. J.; Man, H. W.; Bacheler, L. T.; Rayner, M. M.; Meek, J. L.; Erickson-Viitanen, S.; Jackson, D. A.; Chang H.-C.: Nonpeptide cyclic cyanoguanidines as HIV PR inhibitors: synthesis, structure-activity relationship and X-Ray crystal structure studies; manuscript in preparation.
13. Ganellin, C. R. In Chron. Drug Discovery; Bindra, J. S.; Lednicer, D., Eds., Wiley: New York, 1982, Vol. 1; pp 1-38.
14. Miller, M.; Schneider, J.; Sathyanarayana, B. K.; Toth, M. V.; Marshall, G. R.; Clawson, L.; Seik, L.; Kent, S. B. H.; Wlodawer, A. Science 1989, 1149.
15. Schecter, I.; Berger, A. Biochem. Biophys. Res. Commun. 1967, 27, 157.
16. Pierce, M. E.; Harris, G. D.; Islam, Q.; Radesca, L. A.; Storace, L.; Waltermire, R. E.; Wat, E.; Jadhav, P. K.; Emmett, G. C. J. Org. Chem. 1996, 61, 444.
17. (a) Moynihan, H. A.; Roberts, S. M.; Weldon, H.; Allcock, G. H.; Anggard, E. E.; Warner, T. D. J. Chem. Soc., Perkin Trans. 1 1994, 7, 769.
18. (b) Feldman, P. L. Tetrahedron Lett. 1991, 32, 875.
19. + 612.3226, found 612.3218.
20. + 522.2757, found 522.2741.