QSAR models for 2-amino-6-arylsulfonylbenzonitriles and congeners HIV-1 reverse transcriptase inhibitors based on linear and nonlinear regression methods

European Journal of Medicinal Chemistry

Volumn 44, Issue 5, 2009, Pages 2158-2171

  Hu, Rongjing ^a,b   Doucet, Jean Pierre ^b   Delamar, Michel ^b   Zhang, Ruisheng ^a  

^a LANZHOU UNIVERSITY   (China)

^b UNIVERSITÉ PARIS DIDEROT   (France)

Author keywords

HIV 1 non nucleoside reverse transcriptase inhibitors; NNRTI; PPR; QSAR; SVM

Indexed keywords

ANTIVIRUS AGENT; BENZONITRILE; RNA DIRECTED DNA POLYMERASE INHIBITOR;

ANTIVIRAL ACTIVITY; ARTICLE; ARTIFICIAL NEURAL NETWORK; BINDING AFFINITY; DRUG PROTEIN BINDING; ENZYME BINDING; LINEAR REGRESSION ANALYSIS; NONLINEAR REGRESSION ANALYSIS; PREDICTIVE VALIDITY; PRINCIPAL COMPONENT ANALYSIS; QUANTITATIVE ANALYSIS; STRUCTURE ACTIVITY RELATION; SUPPORT VECTOR MACHINE;

HIV REVERSE TRANSCRIPTASE; NEURAL NETWORKS (COMPUTER); NITRILES; PRINCIPAL COMPONENT ANALYSIS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; REGRESSION ANALYSIS;

EID: 62749144448     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2008.10.021     Document Type: Article

References (57)

1. Marx J.L. Science 217 (1982) 618-621
2. .
3. .
4. Reeves J.D., and Doms R.W. J. Gen. Virol. 83 (2002) 1253-1265
5. De Clercq E. Med. Res. Rev. 22 (2002) 531-565
6. Katz R.A., and Skalka M.A. Annu. Rev. Biochem. 63 (1994) 133-173
7. Esnouf R., Ren J., Ross C., Jones Y., Stammers D., and Stuart D. Nat. Struct. Biol. 2 (1995) 303-308
8. De Clercq E. Antiviral Res. 38 (1998) 153-179
9. Chan J.H., Hong J.S., Hunter III R.N., Orr G.F., Cowan J.R., Sherman D.B., Sparks S.M., Reitter B.E., Andrews III C.W., Hazen R.J., Clair M.St., Boone L.R., Ferris R.G., Creech K.L., Roberts G.B., Short S.A., Weaver K., Ott R.J., Ren J., Stuart A.H.D., and Stammers D.K. J. Med. Chem. 44 (2001) 1866-1882
10. Hansch C., and Fujita T. J. Am. Chem. Soc. 86 (1963) 1616-1626
11. In: Kubinyi H. (Ed). QSAR: Hansch Analysis and Related Approaches (1993), VCH, Weinheim
12. In: Hansch C., and Leo A. (Eds). Exploring QSAR (1995), American Chemical Society, Washington DC
13. Free S.M., and Wilson J.W. J. Med. Chem. 7 (1964) 395-399
14. Randic M. J. Am. Chem. Soc. 97 (1975) 6609-6615
15. In: Kier L.B., and Hall L.H. (Eds). Molecular Connectivity in Structure-Activity Analysis Research (1986), Letchworth, England
16. Crippen G.M. J. Med. Chem. 22 (1979) 988-997
17. Cramer R.D., Patterson D.E., and Bunce J.D. J. Am. Chem. Soc. 110 (1988) 5959-5967
18. Klebe G., Abraham U., and Mietzner T. J. Med. Chem. 37 (1994) 4130-4146
19. Aoyama T., Suzuki Y., and Ichikawa H. J. Med. Chem. 33 (1990) 905-908
20. Aoyama T., Suzuki Y., and Ichikawa H. J. Med. Chem. 33 (1990) 2583-2590
21. Yao X.J., Panaye A., Doucet J.P., Zhang R.S., Chen H.F., Liu M.C., Hu Z.D., and Fan B.T. J. Chem. Inf. Comput. Sci. 44 (2004) 1257-1266
22. Szczurek A., and Maciejewska M. Talanta 64 (2004) 609-617
23. Niwa T. J. Chem. Inf. Comput. Sci. 43 (2003) 113-119
24. Mosier P.D., and Jurs P.C. J. Chem. Inf. Comput. Sci. 42 (2002) 1460-1470
25. De Veaux R.D., Psichogios D.C., and Ungar L.H. Comput. Chem. Eng. 17 (1993) 819-837
26. Xu Q.S., Daszykowskia M., Walczaka B., Daeyaert F., De Jonge M.R., Heeres J., Koymans L.M.H., Lewi P.J., Vinkers H.M., Janssen P.A., and Massart D.L. Chemom. Intell. Lab. Syst. 72 (2004) 27-34
27. Nguyen-Cong V., and Rode B.M. Eur. J. Med. Chem. 31 (1996) 479-484
28. Liu H.X., Zhang R.S., Yao X.J., Liu M.C., Hu Z.D., and Fan B.T. J. Chem. Inf. Comput. Sci. 43 (2003) 1288-1296
29. Liu H.X., Hu R.J., Zhang R.S., Yao X.J., Liu M.C., Hu Z.D., and Fan B.T. J. Comput. Aided Mol. Des. 19 (2005) 33-46
30. Roy K., and Leonard J.T. Bioorg. Med. Chem. 12 (2004) 745-754
31. Leonard J.T., and Roy K. QSAR Comb. Sci. 23 (2004) 23-35
32. Freitas M.P. Org. Biomol. Chem. 4 (2006) 1154-1159
33. Tang L.J., Zhou Y.P., Jiang J.H., Zou H.Y., Wu H.L., Shen G.L., and Yu R.Q. J. Chem. Inf. Model. 47 (2007) 1438-1445
34. Cerius 2, Version 3.5 (1999), Molecular Simulations Inc., San Diego, USA
35. Golbraikh A., and Tropsha A. J. Mol. Graph. Modell. 20 (2002) 269-276
36. Roy P.P., and Roy K. QSAR Comb. Sci. 27 (2008) 302-313
37. HyperChem, Release 7.0 for Windows (2002), Hypercube, Inc.
38. Stewart J.P.P. MOPAC 6.0, Quantum Chemistry Program Exchange, QCPE, No. 455 (1989), Indiana University, Bloomington, IN
39. Dewar M.J.S., Zoebisch E.G., Healy E.F., and Stewart J.J.P. J. Am. Chem. Soc. 107 (1985) 3898-3902
40. .
41. Karelson M. Molecular Descriptors in QSAR/QSPR (2000), Wiley-Interscience, New York
42. Kier L.B., and Hall L.H. Eur. J. Med. Chem. 12 (1977) 307-312
43. Rohrbaugh R.H., and Jurs P.C. Anal. Chim. Acta 199 (1987) 99-109
44. Katritzky A.R., Lobanov V.S., and Karelson M. Comprehensive Descriptors for Structural and Statistical Analysis, Reference Manual, Version 2.0 (1994)
45. Friedman J.H. Ann. Stat. 19 (1991) 1-67
46. Specht D.F. IEEE Trans Neural Networks 2 (1991) 568-576
47. Parzen E. Ann. Math. Stat. 33 (1962) 1065-1076
48. Friedman J.H., and Stuetzle W. J. Am. Stat. Assoc. 76 (1981) 817-823
49. Friedman J.H. Classification and Multiple Regression through Projection Pur-suit. Technical Report LCS 12 (1985), Stanford University, Laboratory for Computational Statistics, Stanford, CA
50. .
51. In: Vapnik V. (Ed). The Nature of Statistical Learning Theory (1995), Springer, New York
52. Vapnik V., Golowich S., and Smola A. Support Vector Method for Function Approximation, Regression Estimation, and Signal Processing. In: Mozer M.C., Jordan M.I., and Petsche T. (Eds). Advances in Neural Information Processing Systems 9 (1997), MIT Press, Cambridge, MA 281-287
53. In: Vapnik V. (Ed). Statistical Learning Theory (1998), Wiley, New York
54. In: Scholkopf B., Burges C., and Smola A. (Eds). Advances in Kernel Methods - Support Vector Learning (1999), MIT Press, Cambridge, MA
55. Gunn S.R., Brown M., and Bossley K.M. Intel. Data Anal. 1208 (1997) 313-323
56. In: Orr M.J.L. (Ed). Introduction to Radial Basis Function Networks (1996), Centre for Cognitive Science, Edinburgh University
57. In: Orr M.J.L. (Ed). MATLAB Routines for Subset Selection and Ridge Regression in Linear Neural Networks (1996), Centre for Cognitive Science, Edinburgh University