Predictive QSAR analysis of anti-HIV agents

Drugs of the Future

Volumn 25, Issue 4, 2000, Pages 393-400

  Mickle, Travis ^a   Nair, Vasu ^a  

^a E11 SSH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2',3' DIDEOXYNUCLEOSIDE DERIVATIVE; ANTIRETROVIRUS AGENT; AZAURACIL; AZAURIDINE; DIDANOSINE; OXETANOCIN A; ZIDOVUDINE;

DRUG ACTIVITY; DRUG CONFORMATION; DRUG STRUCTURE; MOLECULAR MODEL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; REVIEW;

EID: 0034029099     PISSN: 03778282     EISSN: None     Source Type: Journal    
DOI: 10.1358/dof.2000.025.04.858668     Document Type: Review

References (27)

1. De Clercq, E. Toward improved anti-HIV chemotherapy: Therapeutic strategies for intervention with HIV infections. J Med Chem 1995, 38: 2491-517.
2. De Clercq, E. Antiviral therapy of human immunodeficiency virus infections. Clin Microb Rev 1995, 8: 200-39.
3. Jeong, L.S., Kim, H.O., Beach, W.J. et al. Nucleosides and derivatives. In: Anti-AIDS Drug Development: Challenges, Strategies and Prospects. Mohan, P., Baba, M. (Eds.). Harwood Academic: Chur 1995, 39-63.
4. Nair, V., Jahnke, T.S. Antiviral activities of isomeric dideoxynucleosides of D-and L-related families. Antimicrob Agents Chemother 1995, 39: 1017-29.
5. Bagdasarian, C.K., Schramm, V.L., Schwartz, S.D. Molecular electrostatic potential analysis for enzymatic substrates, competitive inhibitors, and transition-state inhibitors. J Am Chem Soc 1996, 118: 8825-36.
6. Nair, V., St. Clair, M., Reardon, J.E. et al. Antiviral, metabolic and pharmacokinetic studies on the isomeric dideoxynucleoside, 4(S)-(6-amino-9H-purin-9-tetrahydro-2(S)-furanmethanol. Antimicrob Agents Chemother 1995, 39: 1993-9.
7. Mickle, T., Nair, V. Correlation of anti-HIV activity with structure: Use of electrostatic potential and conformational analysis. Bioorg Med Chem Lett 1999, 9: 1963-8.
8. Herdewijn, P., Balzarini, J., De Clercq, E. et al. 3'-Substituted 2', 3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents. J Med Chem 1987, 30: 1270-8.
9. De Clercq, E. New selective antiviral agents active against the AIDS virus. TIPS 1987, 8: 339-45.
10. Herdewijn, P., Pauwels, R., Baba, M. et al. Synthesis and anti-HIV activity of various 2' and 3' substituted 2',3'-dideoxyadenosines: A structure activity analysis. J Med Chem 1987, 30: 2131-7.
11. Herdewijn, P., Balzarini, J., Baba, M. et al. Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides. J Med Chem 1988, 31: 2040-8.
12. Balzarini, J., Baba, M., Pauwels, R. et al. Anti-retrovirus activity of 3'-fluoro and 3'-azido-substituted pyrimidine 2',3'-dideoxynucleoside analogues Biochem Pharmacol 1988, 37: 2847-56.
13. Balzarini, J., Van Aeschot, A., Herdewijn, P. et al. 5-Chlorosubstituted derivatives of 2',3'-didehydro-2',3'-dideoxyuridine, 3'-fluoro-2',3'-dideoxyuridine and 3'-azido-2',3'-dideoxyuridine as anti-HIV agents. Biochem Pharmacol 1989, 38: 869-74.
14. Chu, C.K., Schinazi, R.F., Ahn, M.K. et al. Structure-activity relationships of pyrimidine nucleosides as antiviral agents for human immunodeficiency virus type 1 in peripheral mononuclear cells. J Med Chem 1989, 32: 612-7.
15. Lin, T-S., Guo, J-Y., Schinazi, R.F. et al. Synthesis and antiviral activity of various 3'-azido analogues of pyrimidine deoxyhbonucleosides against human immunodeficiency virus (HIV-1, HTLV-III/LAV). J Med Chem 1988, 31: 336-40.
16. Lin, T-S., Luo, M-Z., Liu, M-C. et al. Design and synthesis of 2',3'-dideoxy-2',3'-didehydro-beta-L-5-fluorocytidine (β-L-d4C) and 2',3'-dideoxy-2',3'-didehydro-β-L-fluorocytidine (β-L-Fd4C), two exceptionally potent inhibitors of human hepatitis B virus (HBV) and potent inhibitors of human immunodeficiency virus (HIV) in vitro. J Med Chem 1996, 39: 1757-9.
17. Gosselin, G., Mathe, C., Bergogne, M.C. et al. Enantiomeric 2',3'-dideoxycytidine derivatives are potent human immunodeficiency virus inhibitors in cell cultures. Comptes Rendus Acad Sci III 1994, 317: 85-9.
18. Bolon, P., Wang, P., Chu, C.K. et al. Anti-human immunodeficiency and anti-hepatitis B virus activities of β-L-2',3'-dideoxy purine nucleosides. Bioorg Med Chem Lett 1996, 6: 1657-62.
19. Wang, P., Schinazi, R.F., Chu, C.K. et al. Asymmetric synthesis and anti-HIV activity of L-carbocyclic 2',3'-didehydro-2',3'-dideoxyadenosine. Bioorg Med Chem Lett 1998, 8: 1585-8.
20. Lee, K., Choi, Y., Gullen, E. et al. Synthesis and anti-HIV and anti-HBV activities of 2'-fluoro-2',3'-unsaturated L-nucleosides. J Med Chem 1999, 42: 1320-8.
21. Kotra, L.P., Xiang, Y., Newton, M.G. et al. Structure-activity relationships of 2'-deoxy-2',2'-difluoro-L-erytho-pentofuranosyl nucleosides. J Med Chem 1997, 40: 3635-44.
22. Kim, H.O., Schinazi, R.F., Nampalli, S. et al. 1,3-Dioxolanylpurine nucleosides (2R,4R) and (2R,4S) with selective anti-HIV activity in human lymphocytes. J Med Chem 1993, 36: 30-7.
23. Mansour, T.S., Jin, H.L., Wang, W. et al. Anti-human immunodeficiency virus and anti-hepatitis B virus activities and toxicities of the enantiomers of 2-deoxy-3-oxa-4-thiocytidine and their 5-fluoro analogs in vitro. J Med Chem 1995, 38: 1-4.
24. Kim, H.O., Schinazi, R.F., Shanmuanathan, K. et al. L-β-(2S,4S)-and L-α-(2S,4R)-Dioxolanyl nucleosides as potential anti-HIV agents: Asymmetric synthesis and structure-activity relationships. J Med Chem 1993, 36: 519-28.
25. Seki, J-L., Shimada, N., Takahashi, K. et al. Inhibition of infectivity of HIV by a novel nucleoside, oxetanocin, and related compounds. Antimicrob Agents Chemother 1989, 33, 773-5.
26. Kim, K.H. Non-linear dependence in comparative molecular field analysis (CoMFA). J Comput Aided Mol Des 1993, 7: 71-8.
27. as) of clonidine-like imidazoles, 2-substituted imidazoles, and 1-methyl-2-substituted-imidazotes from 3D structures using a comparative molecular field analysis (CoMFA) approach. J Med Chem 1991, 34: 2056-60.