Synthesis of a non-nucleoside reverse transcriptase inhibitor in the alkenyldiarylmethane (ADAM) series with optimized potency and therapeutic index

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 2, 1998, Pages 195-198

  Cushman, Mark ^a   Casimiro Garcia, Agustin ^a   Williamson, Karen ^b   Rice, William G ^b  

^a PURDUE UNIVERSITY   (United States)

^b SAIC FREDERICK INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

RNA DIRECTED DNA POLYMERASE; RNA DIRECTED DNA POLYMERASE INHIBITOR;

ANTIVIRAL ACTIVITY; ARTICLE; BINDING SITE; CYTOPATHOGENIC EFFECT; CYTOTOXICITY; DRUG SYNTHESIS; ENZYME BINDING; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN;

ANTI-HIV AGENTS; CELL LINE; CYTOPATHOGENIC EFFECT, VIRAL; HIV-1; HUMANS; MODELS, MOLECULAR; REVERSE TRANSCRIPTASE INHIBITORS;

HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 0032548456     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)10214-1     Document Type: Article

References (17)

1. 1. De Clercq, E. Med. Virol. 1996, 6, 97.
2. 2. Artico, M. Farmaco 1996, 51, 305.
3. 3. Havlir, D.; Cheeseman, S. H.; McLaughtin, M.; Murphy, R.; Erice, A.; Spector, S. A.; Greenough, T. C.; Sullivan, J. L.; Hall, D.; Myers, M.; Lamson, M.; Richman, D. D. J. Infect. Dis. 1995, 171, 537.
4. 4. De Clercq, E. Int. J. Immunother. 1994, 10, 145.
5. 5. De Clercq, E. Med. Res. Rev. 1996, 16, 125.
6. 6. Cushman, M.; Golebiewski, M.; Buckheit, R. W. J.; Graham, L.; Rice, W. G. Bioorg. Med. Chem. Lett. 1995, 5, 2713.
7. 7. Cushman, M.; Golebiewski, W. M.; Graham, L.; Turpin, J. A.; Rice, W. G.; Fliakas-Boltz, V.; Buckheit, R. W. Jr, J. Med. Chem. 1996, 39, 3217.
8. 8. Kohlstaedt, L. A.; Wang, J.; Friedman, J. M.; Rice, P. A.; Steitz, T. A. Science 1992, 256, 1783.
9. 9. Ding, J.; Das, K.; Moereels, H.; Koymans, L.; Andries, K.; Janssen, P. A.; Hughes, S. H.; Arnold, E. Nature Struct. Biology 1995, 2, 407.
10. 10. Schäfer, W.; Friebe, W.-G.; Leinert, W.; Mertens, A.; Poll, T.; von der Saal, W.; Zilch, H.; Nuber, H.; Ziegler, M. L. J. Med. Chem. 1993, 36, 726.
11. 11. Bestmann, H. J.; Koschatzky, K. H.; Schätzke, W.; Sub, J.; Vostrowsky, O. Justus Liebigs Ann. Chem. 1981, 1705.
12. 12. Pauwels, R.; Andries, K.; Desmyter, J.; Schols, D.; Kukla, M. J.; Breslin, H. J.; Raeymaeckers, A.; Van Gelder, J.; Woestenborghs, R.; Heykants, J.; Schellekens, K.; Janssen, M. A. C.; De Clercq, E.; Janssen, P. A. J. Nature 1990, 343, 470.
13. 13. Goldman, M. E.; Nunberg, J. H.; O'Brien, J. A.; Quintero, J. C.; Schleif, W. A.; Freund, K. F.; Gaul, S. L.; Saari, W. S.; Wai, J. S.; Huffman, J. M.; Anderson, P. S.; Hupe, D. J.; Emini, E. A.; Stern, A. M. Proc. Natl. Acad. Sci. U. S. A. 1991, 88, 6863.
14. 14. Baba, M.; De Clercq, E.; Tanaka, H.; Ubasawa, M.; Takashima, H.; Sekiya, K.; Nitta, I.; Umezu, K.; Nakashima, H.; Mori, S.; Shigeta, S.; Walker, R. T.; Miyasaka, T. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 2356.
15. 15. Debyser, Z.; Pauwels, R.; Andries, K.; Desmyter, J.; Kukla, M.; Janssen, P. A. J.; De Clercq, E. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 1451.
16. 16. Baizarini, J.; Pérez-Pérez, M.-J.; San-Félix, A.; Camarasa, M.-J.; Bathurst, I. C.; Barr, P. J.; De Clercq, E. J. Biol. Chem. 1992, 267, 11831.
17. 17. Tramontane, E.; Cheng, Y.-c. Biochem. Pharmacol. 1992, 43, 1371.