Quantitative structure-activity relationships and comparative molecular field analysis of TIBO derivatised HIV-1 reverse transcriptase inhibitors

Journal of Computer-Aided Molecular Design

Volumn 13, Issue 6, 1999, Pages 563-577

  Hannongbua, Supa ^a   Pungpo, Pornpan ^a   Limtrakul, Jumras ^a   Wolschann, Peter ^b  

^a KASETSART UNIVERSITY   (Thailand)

^b UNIVERSITY OF VIENNA   (Austria)

Author keywords

3D QSAR; HIV 1; Molecular modeling; NNRTIs; QSAR; Quantum chemical calculations; TIBO derivatives

Indexed keywords

CHEMICAL ANALYSIS; MOLECULAR GRAPHICS; QUANTUM CHEMISTRY;

3D-QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; COMPARATIVE MOLECULAR FIELD ANALYSIS; HIV-1; HIV-1 REVERSE TRANSCRIPTASE; NNRTI; QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP; QUANTUM CHEMICAL CALCULATIONS; QUANTUM-CHEMICAL CALCULATION; TIBO DERIVATIVE;

COMPUTATIONAL CHEMISTRY;

BENZODIAZEPINE DERIVATIVE; RNA DIRECTED DNA POLYMERASE INHIBITOR; TETRAHYDROIMIDAZO[4,5,1 JK][1,4]BENZODIAZEPINONE; UNCLASSIFIED DRUG;

ARTICLE; CELL LINE; COMPUTER AIDED DESIGN; HUMAN IMMUNODEFICIENCY VIRUS 1; MOLECULAR INTERACTION; MOLECULAR MODEL; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; QUANTUM CHEMISTRY;

EID: 0032741707     PISSN: 0920654X     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1008013917905     Document Type: Article

References (31)

1. Pauwels, R., Andries, K., Desmyter, J., Schols, D., Kukla, M.J., Breslin, H.J., Raeymaechers, A., Gelder, J.V., Woestenborghs, R., Heykants, J., Schellekens, K., Janessen, M.A.C., De Clercq, E. and Janssen, P.A.J., Nature, 343 (1990) 470.
2. Frank, K.B., Noll, G.J., Connell, E.V. and Sim, I.S., J. Biol. Chem., 266 (1991) 14232.
3. Althaus, I.W., Chou, J.J., Gonzales, A.J., Deibel, M.R., Chou, K.-C., Kezdy, F.J., Romero, D.L., Aristoff, P.A., Tarpley, W.G. and Reusser, F., J. Biol. Chem., 268 (1993) 6119.
4. Spence, R.A., Kati, W.M., Anderson, K.S. and Johnson, K.A., Science, 267 (1995) 988.
5. Kohlstaedt, L.A., Wang, J., Friedman, J.M., Rice, P.A. and Steitz, T.A., Science, 256 (1992) 1783.
6. Ding, J., Das, K., Tantillo, C., Zhang, W., Clark, A.D.J., Jessen, S., Lu, X., Hsiou, Y., Jacobo-Molina, A., Andries, K., Pauwels, R., Moereels, H., Koymans, L, Janssen, P.A.J., Smith, R.H.J., Kroeger Koepke, R., Michejda, C.J., Hughes, S.H. and Arnold, E., Structure, 3 (1995) 365.
7. Ren, J.S., Esnouf, R., Hopkins, A., Ross, C., Jones, Y., Stammers, D. and Stuart, D., Structure, 3 (1995) 915.
8. Richman, D., Shih, C.-K., Lowy, I., Rose, J., Prodanovich, P., Goff, S. and Griffin, J., Proc. Natl. Acad. Sci. USA, 88 (1991) 11241.
9. Das, K., Ding, J., Hsiou, Y., Clark Jr., A.D., Moereels, H., Koymans, L., Andries, K., Pauwels, R., Janssen, R.A.J., Boyer, P.L., Clark, P., Smith Jr., R.H., Smith, M.B.K., Michejda, C.J., Hughes, S.H. and Arnold, E., J. Mol. Biol., 264 (1996) 1085.
10. Tantillo, C., Ding, J., Jacobo-Molina, A., Nanni, R.G., Boyer, P.L., Hughes, S.H., Pauwels, R., Andries, K., Janssen, P.A.J. and Arnold, E., J. Mol. Biol., 243 (1994) 369.
11. Hannongbua, S., Lawtrakul, L. and Limtrakul, J., J. Comput-Aided Mol. Design, 10 (1996) 145.
12. Hannongbua, S., Lawtrakul, L., Sotriffer, C.A. and Rode, B.M., Quant. Struct.-Act. Relat., 15 (1996) 389.
13. Hansch, C. and Fujita, T., J. Am. Chem. Soc., 86 (1964) 1616.
14. Cramer III, R.D., Patterson, D.E. and Bunce, J.D., J. Am. Chem. Soc., 110 (1988) 5959.
15. Breslin, H.J., Kukla, M.J., Ludovici, D.W., Mohrbacher, R., Ho, W., Miranda, M., Rodgers, J.D., Hitchens, T.K., Leo, G., Gauthier, D.A., Ho, C.Y., Scott, M.K., De Clercq, E., Pauwels, R., Andries, K., Janssen, M.A.C. and Janssen, P.A.J., J. Med. Chem., 38 (1995) 771.
16. Tripos Associates Inc., St. Louis, MO.
17. Dewar, M.J., Zoebisch, E.G., Healy, E.F. and Stewart, J.P., J. Am. Chem. Soc., 107 (1985) 3902.
18. GAUSSIAN 94, Pittsburgh, PA, 1995.
19. ChemPlus 1.0, Hypercube Inc., Waterloo, ON, USA, 1993.
20. Miller, K.J., J. Am. Chem. Soc., 112 (1990) 8533.
21. Norusis, M.J., SPSS for Windows Release 6.0., SPSS, Inc., Chicago, 1993.
22. Quantum Chemistry Program Exchange, Indiana University, Bloomington, IN.
23. SYBYL Molecular Modelling Software, version 6.4, Tripos Associates, Inc., St. Louis, MO. 1996.
24. Wold, S., Johansson, E. and Cocchi, M., In Kubinyi, H. (Ed.) 3D QSAR in Drug Design: Theory, Methods and Applications, ESCOM, Leiden, 1993, pp. 523-549.
25. SYBYL Molecular Modelling Software, version 6.3, SYBYL Ligand Base Design, Tripos Associates, Inc., St. Louis, MO, 1996, p. 229.
26. Topliss, J.G. and Costello, R.J., J. Med. Chem., 15 (1972) 1066.
27. Wold, S., Quant. Struct.-Act. Relat., 10 (1991) 191.
28. Ho, W., Kukla, M.J., Breslin, H.J., Lodevici, D.W., Grows, P.P., Diamond, C.J., Miranda, M., Rodgers, D.W., Ho, C.Y, De Clercq, E., Pauwels, R., Andries, K., Janssen, M.A.C. and Janssen, P.A.J., J. Med. Chem., 38 (1995) 794.
29. Kukla, M.J., Breslin, H.J., Diamond, C.J., Grods, P.P., Ho, C.Y., Miranda, M., Roders, J.D., Sherril, R.G., De Clercq, E. and Janssen, P.A.J., J. Med. Chem., 34 (1991) 3187.
30. Kukla, M.J., Breslin, H.J., Pauwels, R., Fedde, C.L., Scott, M.K., Miranda, M., Sherril, R.G., Raeymaeker, A., Gelder, J.V., Andries, K., Janssen, M.A.C., De Clercq, E. and Janssen, P.A.J., J. Med. Chem., 34 (1991) 746.
31. Hansch, C. and Leo, A., Substituent Constants for Correlation Analysis in Chemistry and Biology, Wiley Interscience, New York, NY, 1979.