Classical QSAR modeling of CCR5 receptor binding affinity of substituted benzylpyrazoles

QSAR and Combinatorial Science

Volumn 23, Issue 6, 2004, Pages 387-398

  Leonard, J Thomas ^a   Roy, Kunal ^a  

^a JADAVPUR UNIVERSITY   (India)

Author keywords

AM1 calculations; Anti HIV activity; Benzylpyrazoles; CCR5 receptor binding affinity; QSAR

Indexed keywords

BINDING ENERGY; COMPUTATIONAL CHEMISTRY; REGRESSION ANALYSIS;

AM1 CALCULATIONS; ANTI-HIV ACTIVITY; BENZYLPYRAZOLE; BINDING AFFINITIES; CCR5 RECEPTOR BINDING AFFINITY; QSAR; QSAR MODELING; QSAR STUDIES; RECEPTOR BINDING; TYPE ANALYSIS;

PRINCIPAL COMPONENT ANALYSIS;

BENZYL DERIVATIVE; BENZYLPYRAZOLE DERIVATIVE; CHEMOKINE RECEPTOR CCR5; PHENYL GROUP; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ACQUIRED IMMUNE DEFICIENCY SYNDROME; ARTICLE; BINDING AFFINITY; CALCULATION; CHEMICAL ANALYSIS; DRUG RECEPTOR BINDING; ELECTRICITY; ELECTRONICS; FUJITA BAN ANALYSIS; GEOMETRY; HANSCH ANALYSIS; HYDROPHOBICITY; LIGHT REFRACTION; MULTIPLE REGRESSION; PHYSICAL CHEMISTRY; PRINCIPAL COMPONENT ANALYSIS; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STATISTICAL ANALYSIS; STEREOSPECIFICITY; VALIDATION PROCESS;

EID: 8544262940     PISSN: 1611020X     EISSN: None     Source Type: Journal    
DOI: 10.1002/qsar.200430871     Document Type: Article

References (39)

1. http://www.unaids.org/Unaids/EN/Resources/Publications
2. S. A. Mehanna, Rationale of Design of Anti-HIV Drugs, in: D. J. Abraham (Ed.), Burger's Medicinal Chemistry and Drug Discovery, John Wiley & Sons, New York 2003, pp. 458-483.
3. E. A. Berger, P. M. Murphy, J. M. Farber, Annu. Rev. Immunol. 1999, 17, 657-700.
4. http://www.euroscreen.be/PRESSRELEASES/press_10_09_02.html
5. W. A. Paxton, R. Liu, S. Kang, L. Wu, T. R. Gingeras, N. R. Landau, C. R. Mackay, R. A. Koup. Virology. 1998, 244, 66-73.
6. F. Tsamis, S. Gavrilov, F. Kajumo, C. Seibert, S. Kuhmann, T. Ketas, A. Trkola, A. Palani, J. W. Clader, J. R. Tagat, S. McCombie, B. Baroudy, J. P. Moore, T. P. Sakmar, T. Dragic, J. Virol. 2003, 77, 5201-5208.
7. J. M. Kilby, J. J. Eron, N. Eng. J. Med. 2003, 348, 2228-2238.
8. J. M. Farber, E. A. Berger, Proc. Natl. Acad. Sci. USA. 2002, 99, 1749-1751.
9. D. D. Richman, Nature. 2001, 410, 995-1001.
10. W. Kazmierski, N. Bifulco, H. Yang, L. Boone, F. DeAnda, C. Watson, T. Kenakin, Bioorg. Med. Chem. 2003, 11, 2663-2676.
11. M. Samson, M. Parmentier, G. Vassart, F. Libert, US Patent No. 6,448,375 B1, Sept. 10, 2002.
12. W. E. Bondinell, V. A. Reader, T. W. Fu Ku, US Patent No. 6,242,459 B1, June 05, 2001.
13. J. W. Clader, S.-I. Y. Lin, S. W. Mc. Combe, P. B. Pushpavanam, S. Vice, US Patent No. 6,689,783 B2, February 10, 2004.
14. M. Song, C. M. Breneman, M. Sukumar, Bioorg. Med. Chem. 2004, 12, 489-499.
15. A. K. Debnath, A. K. J. Med. Chem. 2003, 46, 4501-4515.
16. D. Shen, M. Shu, C. A. Willoughby, S. Shah, C. L. Lynch, J. J. Hale, S. G. Mills, K. T. Chapman, L. Malkowitz, M. S. Springer, S. L. Gould, J. A. DeMartino, S. J. Siciliano, K. Lyons, J. V. Pivnichny, G. Y. Kwei, A. Carella, G. Carver, K. Holmes, W. A. Schleif, R. Danzeisen, D. Hazuda, J. Kessler, J. Lineberger, M. D. Miller, E. A. Emini, Bioorg. Med. Chem. Lett. 2004, 14, 941-945.
17. M. Shu, J. L. Loebach, K. A. Parker, S. G. Mills, K. T. Chapman, D. Shen, L. Malkowitz, M. S. Springer, S. L. Gould, J. A. DeMartino, S. J. Siciliano, J. Di Salvo, K. Lyons, J. V. Pivnichny, G. Y. Kwei, A. Carella, G. Carver, K. Holmes, W. A. Schleif, R. Danzeisen, D. Hazuda, J. Kessler, J. Lineberger, M. D. Miller, E. A. Emini, Bioorg. Med. Chem. Lett. 2004, 14, 947-52.
18. T. Fujita, T. Ban, J. Med. Chem. 1971, 14, 148-152.
19. H. Kubinyi, O. H. Kehrhahn, J. Med. Chem. 1976, 19, 1040-1049.
20. H. Kubinyi, O. H. Kehrhahn, J. Med. Chem. 1976, 19, 578-586.
21. H. Kubinyi, J. Med. Chem. 1976, 19, 587-600.
22. C. Hansch, T. Fujita, J. Am. Chem. Soc. 1964, 86, 1616-1626.
23. C. Hansch, A. Leo, D. Hoekman, in: Exploring QSAR. Hydrophobic, Electronic and Steric Constants, American Chemical Society: Washington, DC, 1995.
24. M. J. S. Dewar, E. G. Zoebisch, E. F. Healey, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902-3909.
25. M. J. S. Dewar, C. H. Hwang, D. R. Kuhn, J. Am. Chem. Soc. 1991, 113, 735-741.
26. P. U. Civcir, J. Mol. Struct.: THEOCHEM., 2001, 535, 121-129.
27. Chem 3D Pro version 5.0 is a program of CambridgeSoft Corporation, MA, U.S.A.
28. K. Roy. A. U. De, C. Sengupta, Quant. Struct.-Act. Relat. 2001, 20, 319-326.
29. K. Roy, QSAR Comb. Sci. 2003, 22, 614-621.
30. J. T. Leonard, K. Roy, QSAR Comb. Sci. 2004, 23, 23-35.
31. 2 version 4.8 is a product of Accelrys. Inc., San Diego, USA.
32. R. Franke, Theoretical Drug Design Methods, Elsevier, Amsterdam 1984, pp. 184-195.
33. R. Franke, A. Gruska, Principal component and factor analysis, in: H. van de Waterbeemd, (Ed.), Chemometric Methods in Molecular Design, VCH, Weinheim 1995, pp. 113-163.
34. SPSS is a statistical software of SPSS Inc., IL, USA.
35. G. W. Snedecor, W. G. Cochran,. Statistical Methods, Oxford & IBH Publishing Co. Pvt. Ltd., New Delhi 1967, pp. 381-418.
36. S. Wold, L. Eriksson, Statistical Validation of QSAR Results, in: H. van de Waterbeemd, (Ed), Chemometric Methods in Molecular Design, VCH, Weinheim 1995, pp. 312-317.
37. A. K. Debnath, Quantitative Structure-Activity Relationship (QSAR): A Versatile Tool in Drug Design, in: A. K. Ghose, V. N. Viswanadhan, (Eds.), Combinatorial Library design and Evaluation, Marcel Dekker, Inc. New York 2001, pp. 73-129.
38. J. D. Walker, J. Jaworska, M. H. Comber, T. W. Schultz, J. C. Dearden, Environ. Toxicol. Chem. 2003, 22, 1653-1665.
39. L. Eriksson, J. Jaworska, A. P. Worth, M. T. D. Cronin, R. M. McDowell, P. Gramatica, Environ. Health Perspect. 2003, 111, 1361-1375.