Chemistry and Structure-Activity Relationship of HIV-1 Integrase Inhibitor Integracide B and Related Natural Products

Journal of Natural Products

Volumn 66, Issue 10, 2003, Pages 1338-1344

  Singh, Sheo B ^a   Ondeyka, John G ^a   Schleift, William A ^a   Felock, Peter ^a   Hazuda, Daria J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; ANTIFUNGAL AGENT; ANTIRETROVIRUS AGENT; CARBOXYL GROUP; CLAVARIC ACID; CLAVARINONE; ELASTASE INHIBITOR; FUNCTIONAL GROUP; INTEGRACIDE A; INTEGRACIDE B; INTEGRASE INHIBITOR; NATURAL PRODUCT; SULFATE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DERIVATIZATION; ENZYME INHIBITION; FUSARIUM; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; STRUCTURE ACTIVITY RELATION; VIRUS DNA CELL DNA INTERACTION; VIRUS REPLICATION;

ANTI-HIV AGENTS; COMBINATORIAL CHEMISTRY TECHNIQUES; HIV INTEGRASE; HIV INTEGRASE INHIBITORS; HIV-1; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; TRITERPENES;

FUSARIUM; HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1; RNA VIRUSES;

EID: 0142218979     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np030211s     Document Type: Article

References (27)

1. For recent reviews on HIV integrase, see: (a) Craigie, R. J. Biol. Chem. 2001, 276, 23213-23216.
2. (b) Esposito, D.; Craigie, R. Adv. Virus Res. 1999, 52, 319-333.
3. (c) Neamati, N. Exp. Opin. Invest. Drugs 2003, 12, 289-292.
4. (d) Neamati, N. Exp. Opin. Ther. Patents 2002, 12, 709-724.
5. (e) Neamati, N. Exp. Opin. Invest. Drugs 2001, 10, 281-296.
6. (f) Pais, G. C. G.; Burke, J. T. R. Drugs Future 2002, 27, 1101-1111.
7. (g) De Clercq, E. Med. Res. Rev. 2002, 22, 531-565.
8. (a) Hazuda, D. J.; Felock, P.; Witmer, M.; Wolfe, A.; Stillmock, K.; Grobler, J. A.; Espeseth, A.; Gabryelski, L.; Schleif, W.; Blau, C.; Miller, M. D. Science 2000, 287, 646-650.
9. (b) Wai, J. S.; Egbertson, M. S.; Payne, L. S.; Fisher, T. E.; Embrey, M. W.; Tran, L. O.; Melamed, J. Y.; Langford, H. M.; Guare, J. P.; Zhuang, L.; Grey, V. E.; Vacca, J. P.; Holloway, M. K.; Naylor-Olsen, A. M.; Hazuda, D. J.; Felock, P. J.; Wolfe, A. L.; Stillmock, K. A.; Schleif, W.; Gabryelski, L. J.; Young, S. D. J. Med. Chem. 2000, 43, 4923-4926, and references therein.
10. (c) Pais, G. C. G.; Burke, J. T. R. Drugs Future 2002, 27, 1101-1111.
11. (a) Singh, S. B.; Zink, D. L.; Goetz, M. A.; Dombrowski, A. W.; Polishook, J. D.; Hazuda, D. L. Tetrahedron Lett. 1998, 39, 2243-2246.
12. (b) Hazuda, D.; Blau, C. U. C.; Felock, P.; Hastings, J.; Pramanik, B.; Wolfe, A.; Bushman, F.; Farnet, C.; Goetz, M.; Williams, M.; Silverman, K.; Lingham, R.; Singh, S. Antiviral Chem. Chemother. 1999, 10, 63-70.
13. Singh, S. B.; Zink, D.; Polishook, J.; Valentino, D.; Shafiee, A.; Silverman, K.; Felock, P.; Teran, A.; Vilella, D.; Hazuda, D. J.; Lingham, R. B. Tetrahedron Lett. 1999, 40, 8775-8779.
14. (b) Singh, S. B.; Felock, P.; Hazuda, D. J. Bioorg. Med. Chem. Lett. 2000, 10, 235-237.
15. Singh, S. B.; Jayasuriya, H.; Salituro, G. M., Zink, D. L.; Shafiee, A.; Heimbuch, B.; Silverman, K. C.; Lingham, R. B.; Genilloud, O.; Teran, A.; Vilella, D.; Felock, P.; Hazuda, D. J. Nat. Prod. 2001, 64, 874-882.
16. Singh, S. B.; Zink, D.; Bills, G. F.; Pelaez, F.; Teran, A.; Collado, J. ; Silverman, K.; Lingham, R. B.; Felock, P.; Hazuda, D. J. Tetrahedron Lett. 2002, 43, 1617-1620.
17. Singh, S. B.; Zink, D.; Quamina, D. S.; Pelaez, F.; Teran, A.; Felock, P.; Hazuda, D. J. Tetrahedron Lett. 2002, 43, 2351-2354.
18. Singh, S. B.; Zink, D.; Heimbach, B.; Genilloud, O.; Teran, A.; Silverman, K.; Lingham, R. B.; Felock, P.; Hazuda, D. J. Org. Lett. 2002, 4, 1123-1126.
19. Singh, S. B.; Zink, D.; Bills, G. F.; Teran, A.; Silverman, K.; Lingham, R. B.; Felock, P.; Hazuda, D. J. Bioorg. Med. Chem. Lett. 2003, 13, 713-717.
20. Singh, S. B.; Zink, D.; Dombrowski, A. W.; Polishook, J. D.; Ondeyka, J. G.; Hirshfield, J.; Felock, P.; Hazuda, D. J. Bioorg. Med. Chem. 2003, 11, 1577-1582.
21. (a) Burg, R. W.; Dulaney, E. L.; Hensens, O. D.; Liesch, J. M.; Ondeyka, J. G.; Wichman, C. F. (Merck & Co., Inc.) US 4871727 (October 3, 1989).
22. (b) Ashe, B. M.; Fletcher, D. S. (Merck & Co., Inc.) US 4874755 (October 17, 1989).
23. Jayasuriya, H. J.; Silverman, K. C.; Zink, D. L.; Jenkins, R. G.; Sanchez, M.; Pelaez, F.; Vilella, D.; Lingham, R. B.; Singh, S. B. J. Nat. Prod. 1998, 61, 1568-1570.
24. Singh, S. B. Tetrahedron Lett. 2000, 41, 6973-6976.
25. Singh, S. B.; Zink, D. L.; Liesch, J. M.; Moseley, R. T.; Dombrowski, A. W.; Bills, G. F.; Darkin-Rattray, S. J.; Schmatz, D. M.; Goetz, M. A. J. Org. Chem. 2002, 67, 815-825.
26. LaFemina, R. L.; Graham, P. L.; LeGrow, K.; Hastings, J. C.; Wolfe, A.; Young, S. D.; Emini, E. A.; Hazuda, D. J. Antimicrob. Agents Chemother. 1995, 39, 320-324.
27. Farnet, C. M.; Wang, B.; Lipford, J. R.; Bushman, F. D. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 9742-9747.