3D-QSAR CoMFA/CoMSIA studies on 5-aryl-2,2-dialkyl-4-phenyl-3(2H)-furanone derivatives, as selective COX-2 inhibitors

Acta Pharmaceutica

Volumn 56, Issue 2, 2006, Pages 157-174

  Puntambekar, Devendra Sharad ^a   Giridhar, Rajani ^a   Yadav, Mange Ram ^a  

^a NONE

Author keywords

3D QSAR; Anti inflammatory agents; CoMFA; CoMSIA; Cyclooxygenase 2 inhibitors

Indexed keywords

4 PHENYL 3 (2H) FURANONE DERIVATIVE; CYCLOOXYGENASE 2 INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; CONTROLLED STUDY; DRUG STRUCTURE; ELECTRICITY; HUMAN; HYDROGEN BOND; HYDROPHOBICITY; MOLECULAR MODEL; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

EID: 33645551958     PISSN: 13300075     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (25)

1. P. Mantri and D. Witiak, Inhibitors of COX and 5-Lipoxygenase, Curr. Med. Chem. 1 (1994) 328-355.
2. J. R. Vane and R. Botting, Mechanism of action of anti-inflammatory drugs, Scand. T. Rheumatol. Suppl. 102 (1996) 9-21.
3. W. L. Smith, P. Borgeat and F. A. Fitzpatrik, The Eicosanoids: COX, Lipoxygenase and Epoxygenase Pathways, in Biochemistry of Lipids, Lipoproteins and Membranes (Ed. D. E. Vance), Elsevier, New York 1991, pp. 297-325.
4. W. Xie, J. Chipman, D. L. Robertson, R. L. Erikson and D. L. Simmons, Expression of mitogen response gene encoding prostaglandin synthase regulated by mRNA splicing, Proc. Natl. Acad. Sci. U.S.A. 88 (1991) 2692-2696.
5. J. R. Vane and R. M. Botting, Antiinflammatory drugs and their mechanism of action, Inflammation Res. 47 (1998) S78-S87.
6. M. Katori and M. Majima, Possible background mechanisms of the effectiveness of COX-2 inhibitors in treatment of rheumatoid arthritis, Inflammation Res. 47 (1998) S107-S111.
7. D. L. Dewitt, COX-2 Inhibitors: The super new aspirins, Mol. Pharmacol. 4 (1999) 625-631.
8. L. J. Marnett and A. S. Kalgutkar, Design of selective inhibitors of COX-2 as non-ulcerogenic antiinflammatory agents, Curr. Opin. Chem. Biol. 2 (1998) 482-490.
9. C. J. Hawkey, COX-2 Inhibitors, Lancet 353 (1999) 307-314.
10. J. R. Vane and R. Botting, Clinical Significance and Potential of Selective COX-2 Inhibition, William Harvey Press, London 1998.
11. R. G. Kurumbail, A. M. Stevens, J. K. Gierse, J. J. McDonald, R. A. Slegeman, J. Y. Pak, D. I. Gildehaus, J. M. Miyashiro, T. D. Penning, K. Siebert, P. C. Isakson and W. C. Stallings, Structural basis of selective inhibition of COX-2 by anti-inflammatory agents, Nature 384 (1996) 644-648.
12. Y. Leblanc, W. C. Black, C. C. Chan, S. Charleson, D. Delorme, D. Denis, J. Y. Gautheir, E. L. Grimm, R. Gardon, D. Guay, P. Hamel, S. Kargman, C. K. Lau, J. I. Mancini, M. Quellet, D. Percival, P. Roy, K. Skorey, P. Tagari, E. Wong, L. Xu and P. Prasit, Synthesis and biological evaluation of both enantiomers of L-761000 as inhibitors of cyclooxygenase-1 and 2, Bioorg. Med. Chem. Lett. 6 (1996) 731-736.
13. K. M. Woods, R. W. McCroskey and M. R. Michaelides, Heterocyclic compounds as COX-2 inhibitors, World Patent WO989330, 4 March 1997.
14. T. Klein, R. M. Nusing, J. Pfeilschifetr and V. Ulrich, Selective inhibition of COX-2, Biochem. Pharmacol. 48 (1994) 1605-1610.
15. P. Chavatte, S. Yous, C. Maro, N. Baurin and D. Lesieur, Three dimensional quantitative structure activity relationships of cyclooxygenase-2: A comparative molecular field analysis, J. Med. Chem. 44 (2001) 3223-3230.
16. J. R. Desiraju, B. Gopalkrishnan, R. K. R. Jetti, A. Nagaraju, D. Ravindra, J. R. P. Sarma and M. E. Sobhia, Computer aided drug design of selective COX-2 inhibitors: CoMFA, CoMSIA and docking studies of some 1,2 diarylimidazole derivatives, J. Med. Chem. 45 (2002) 4847-4855.
17. H. Liu, X. Q. Huang, S. J. Shen, X. M. Luo, M. H. Li, B. Xiong, G. Chen, J. K. Shen, Y. M. Yang and K. X. Chen, Inhibitory mode of 1,5 diarylpyrazole derivatives against cyclooxygenase-2 and cyclooxygenase-1, J. Med. Chem. 45 (2002) 4816-4827.
18. R. Solvia, C. Almansa, S. G. Kalko, S. J. Luque and M. Brozco, Theoretical studies on the inhibition mechanisms of COX-2: Is there a unique recognition site? J. Med. Chem. 46 (2003) 1372-1377.
19. R. Garg, A. Kurup, S. B. Mekapati and C. Hansch, Cyclooxygenase inhibition: A comparative QSAR study, Chem. Rev. 102 (2003) 703-732.
20. E. J. Topol, Failing the public health - Rofecoxib, Merck and the FDA, New Engl. J. Med. 351 (2004) 1707-1709.
21. S. S. Shin, Y. Byun, K. M. Lim, J. K. Choi, K. Lee, J. H. Mon, J. K. Kim, Y. S. Jeong, J. Y. Kim, H. J. Koh, Y. H. Park, M. S. Noh and S. Chung, In vitro SAR and in vivo studies for a novel class of COX-2 inhibitors: 5-aryl-2,2 dialkyl-4-phenyl-3(2H) furanone derivatives, J. Med. Chem. 47 (2004) 792-804.
22. SYBYL 6.9, Tripos Associates, St. Louis, MO, USA.
23. M. Clark, R. R. Crammer and O. N. Van, The tripos force field, J. Comput. Chem. 10 (1989) 982-1012.
24. J. James and P. Stewart MOPAC: A semi empirical molecular orbital program, J. Comput. Aid. Mol. Des. 4 (1990) 1-103.
25. S. Wold, C. Albano, W. Dunn, U. Edlund, K. Esbensen, P. Geladi, S. Hellberg, E. Johansson, W. Lindberg and M. Sjosstrom, Mathematics and Statistics in Chemistry, in Chemometrics (Ed. B. Kowalski), Reidel, Dordrecht 1987, pp. 17.