HEPT derivatives as non-nucleoside inhibitors of HIV-1 reverse trancriptase: QSAR studies agree with the crystal structures

Journal of Computer-Aided Molecular Design

Volumn 16, Issue 4, 2002, Pages 287-295

  Gaudio, Anderson Coser ^a   Montanari, Carlos Alberto ^b  

^a FEDERAL UNIVERSITY OF ESPÍRITO SANTO   (Brazil)

^b FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

Author keywords

Acyclouridine derivatives; Human immunodeficiency virus type 1; Molecular modeling; Quantitative structure activity relationships; Reverse transcriptase

Indexed keywords

BIOMOLECULES; COMPUTATIONAL CHEMISTRY; CRYSTAL STRUCTURE; VIRUSES;

ACTIVE SITE; ACYCLOURIDINE DERIVATIVE; CRYSTALS STRUCTURES; HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS TYPE 1; PHENYLTHIO; QSAR STUDIES; QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP; REVERSE-TRANSCRIPTASE; SYNTHESISED;

DISEASES;

1 [(2 HYDROXYETHOXY)METHYL] 6 (PHENYLTHIO)THYMINE; HYDROCARBON SUBSTITUENT; RNA DIRECTED DNA POLYMERASE INHIBITOR; RNA DIRECTED RNA POLYMERASE;

ACQUIRED IMMUNE DEFICIENCY SYNDROME; AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG BINDING SITE; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS 1; MOLECULAR MODEL; PREDICTION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; VALIDATION PROCESS;

EID: 0036554692     PISSN: 0920654X     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1020280627193     Document Type: Article

References (37)

1. Pedersen, O.S. and Pedersen, E.B., Antivir. Chem. Chemother., 10 (1999) 285.
2. De Clercq, E., Farmaco, 54 (1999) 26.
3. De Clercq, E., Antiviral Res., 38 (1998) 153.
4. Molla, A. and Japour, A., Curr. Opin. Infect. Dis., 10 (1997) 491.
5. Flexner, C.N., Engl. J. Med., 338 (1998) 1281.
6. Patick, A.K. and Potts, K.E., Clin. Microbiol. Rev., 11 (1998) 614.
7. Kakuda, T.N., Struble, K.A. and Piscitelli, S.C., Am. J. Health-Syst. Pharm., 55 (1998) 233.
8. Rana, K.Z. and Dudley, M.N., Pharmacotherapy, 19 (1999) 35.
9. Miyasaka, T., Tanaka, H., Baba, M., Hayakawa, H., Walker, R.T., Balzarini, J. and De Clercq, E., J. Med. Chem., 32 (1989) 2507.
10. Tanaka, H., Baba, M., Hayakawa, H., Sakamaki, T., Miyasaka, T., Ubasawa, M., Takashima, H., Sekiya, K., Nitta, I., Shigeta, S., Walker, R.T., Balzarini, J. and De Clercq, E., J. Med. Chem., 34 (1991) 349.
11. Tanaka, H., Baba, M., Ubasawa, M., Takashima, H., Sekiya, K., Nitta, I., Shigeta, S., Walker, R.T., De Clercq, E. and Miyasaka, T., J. Med. Chem., 34 (1991) 1394.
12. Tanaka, H., Takashima, H., Ubasawa, M., Sekiya, K., Inouye, N., Baba, M., Shigeta, S., Walker, R.T., De Clercq, E. and Miyasaka, T., J. Med. Chem., 38 (1995) 2860.
13. Tanaka, H., Baba, M., Yamamoto, T., Mori, S., Walker, R.T., De Clercq, E. and Miyasaka, T., Bioorg. Med. Chem. Lett., 3 (1993) 1681.
14. Tanaka, H., Takashima, H., Ubasawa, M., Sekiya, K., Nitta, I., Baba, M., Shigeta, S., Walker, R.T., De Clercq, E. and Miyasaka, T., J. Med. Chem., 35 (1992) 4713.
15. Tanaka, H., Takashima, H., Ubasawa, M., Sekiya, K., Nitta, I., Baba, M., Shigeta, S., Walker, R.T., De Clercq, E. and Miyasaka, T., J. Med. Chem., 35 (1992) 337.
16. Hopkins, A.L., Ren, J., Esnouf, R.M., Willcox, B.E., Jones, E.Y, Ross, C., Miyasaka, T., Walker, R.T., Tanaka, H., Stammers, D.K. and Stuart, D.I., J. Med. Chem., 39 (1996) 1589.
17. Ren, J.S., Esnouf, R., Garman, E., Somers, D., Ross, C., Kirby, I., Keeling, J., Darby, G., Jones, Y, Stuart, D. and Stammers, D., Nature Struct. Biol., 2 (1995) 293.
18. Hansch, C. and Zhang, L.T., Bioorg. Med. Chem. Lett., 2 (1992) 1165.
19. Hannongbua, S., Lawtrakul, L., Sotriffer, C.A. and Rode, B.M., Quant. Struct.-Act. Relat., 15 (1996) 389.
20. Hannongbua, S., Lawtrakul, L. and Limtrakul, J., J. Comput.-Aided Mol. Des., 10 (1996) 145.
21. Garg, R., Kurup, A. and Gupta, S.P., Quant. Struct.-Act. Relat., 16 (1997) 20.
22. Kireev, D.B., Chrétien, J.R., Grierson, D.S. and Monneret, C., J. Med. Chem., 40 (1997) 4257.
23. Luco, J.M. and Ferretti, F.H., J. Chem. Inf. Comp. Sci., 37 (1997) 392.
24. Tronchet, J.M.J., Grigorov, M., Dolatshahi, N., Moriaud, F. and Weber, J., Eur. J. Med. Chem., 32 (1997) 279.
25. Garg, R., Gupta, S.P., Gao, H., Babu, M.S., Debnath, A.K. and Hansch, C., Chem. Rev., 99 (1999) 3525.
26. Lawtrakul, L. and Hannongbua, S., Sci. Pharm., 67 (1999) 43.
27. Jalali-Heravi, M. and Parastar, F., J. Chem. Inf. Comp. Sci., 40 (2000) 147.
28. Alves, C.N., Pinheiro, J.C., Camargo, A.J., Ferreira, M.M.C. and Da Silva, A.B.F., J. Mol. Struct. (Theochem), 530 (2000) 39.
29. Hannongbua, S., Nivesanond, K., Lawtrakul, L., Pungpo, P. and Wolschann, P., J. Chem. Inf. Comp. Sci., 41 (2001) 848.
30. De Oliveira, D.B. and Gaudio, A.C., Quant. Struct.-Act. Relat., 19 (2000) 599.
31. Berman, H.M., Westbrook, J., Feng, Z., Gilliland, G., Bhat, T.N., Weissig, H., Shindyalov, I.N. and Bourne, P.E., Nucl. Acids Res., 28 (2000) 235.
32. BioMedCAChe 5.0, Fujitsu Ltd., Tokio, 2000.
33. WebLab Viewer Pro 4.0, Molecular Simulations, Inc., San Diego-CA, 2000.
34. Fujita, T., Hansch, C. and Iwasa, J., J. Am. Chem. Soc., 86 (1964) 5175.
35. R. Mannhold, P. Krogsgaard-Larsen and H. Timmerman (Eds.), QSAR: Hansch Analysis and Related Approaches, Vol. 1, VCH, Weinheim, 1993.
36. Taft, R.W., Jr., J. Am. Chem. Soc., 74 (1952) 3120.
37. Tanaka, H., Baba, M., Takahashi, E., Matsumoto, K., Kittaka, A., Walker, R.T., De Clercq, E. and Miyasaka, T., Nucleosides Nucleotides, 13 (1994) 155.