Methanesulfonamide group at position-4 of the C-5-phenyl ring of 1,5-diarylpyrazole affords a potent class of cyclooxygenase-2 (COX-2) inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 7, 2004, Pages 1683-1688

  Singh, Sunil Kumar ^a   Vobbalareddy, Saibaba ^a   Shivaramakrishna, Samala ^a   Krishnamraju, A ^a   Rajjak, Shaikh Abdul ^a   Casturi, Seshagiri Rao ^a   Akhila, Vangoori ^a   Rao, Yeleswarapu Koteswar ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

Author keywords

1,5 diarylpyrazoles; Cyclooxygenase 2 inhibitors; Methanesulfonamide

Indexed keywords

CELECOXIB; CYCLOOXYGENASE 2 INHIBITOR; ETORICOXIB; INDOMETACIN; NIMESULIDE; PHENYL GROUP; PYRAZOLE DERIVATIVE; ROFECOXIB; SULFONAMIDE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG POTENCY; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; IN VITRO STUDY; IN VIVO STUDY; NONHUMAN; PAW EDEMA; RAT; SEMINAL VESICLE; STRUCTURE ACTIVITY RELATION;

CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; CYCLOOXYGENASE INHIBITORS; HUMANS; ISOENZYMES; MEMBRANE PROTEINS; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; PYRAZOLES; SULFONAMIDES;

EID: 1542613875     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.01.053     Document Type: Article

References (34)

1. Vane J.R., Bakhle Y.S., Botting R.M. Annu. Rev. Pharmacol. Toxicol. 38:1998;97.
2. Picot D., Loll P.J., Garavito R.M. Nature. 367:1994;243.
3. Wallace J.L. Am. J. Med. 107:1999;11. S.
4. Xie W., Chipman J.G., Robertson D.L., Erikson R.L., Simmons D.L. Proc. Natl. Acad. Sci. U.S.A. 88:1991;2692.
5. Moncada S., Gryglewski R., Bunting S., Vane J.R. Nature. 263:1976;663.
6. Whittle B.J.R., Higgs G.A., Eakins K.E., Moncada S., Vane J.R. Nature. 284:1980;271.
7. Allison M.C., Howatson A.G., Torrance C.J., Lee F.D., Russel R.I.G. N. Engl. J. Med. 327:1992;749.
8. Xie W., Robertson D.L., Simmons D.L. Drug Develop. Res. 25:1992;249.
9. Vane J. Nature. 367:1994;215.
10. Griswold D.E., Adams J.L. Med. Res. Rev. 16:1996;181.
11. Meyer-irchrath J., Schror K. Curr. Med. Chem. 7:2000;1121. and references cited therein.
12. Penning T.D., Talley J.J., Bertenshaw S.R., Carter J.S., Collins P.W., Docter S., Graneto M.J., Lee L.F., Malecha J.W., Miyashiro J.M., Rogers R.S., Rogier D.J., Yu S.S., Anderson G.D., Burton E.G., Cogburn J.N., Gregory S.A., Koboldt C.M., Perkins W.E., Seibert K., Veenhuizen A.M., Zhang Y.Y., Isakson P.C. J. Med. Chem. 40:1997;1347.
13. Prasit P., Wang Z., Brideau C., Chan C.-C., Charleson S., Cromlish W., Either D., Evans J.F., Ford-Hutchinson A.W., Gauthier J.Y., Gordon R., Guay J., Gresser M., Kargman S., Kennedy B., Leblanc Y., Leger S., Mancini J., O'Neil G.P., Ouellet M., Percival M.D., Perrier H., Riendeau D., Rodger I., Tagari P., Therien M., Vickers P., Wong E., Xu L.-J., Young R.N., Zamboni R., Boyce S., Rupniak N., Forrest M., Visco D., Patrick D. Bioorg. Med. Chem. Lett. 9:1999;1773.
14. Talley J.J., Brown D.L., Carter J.S., Graneto M.J., Koboldt C.M., Masferrer J.L., Perkins W.E., Rogers R.S., Shaffer A.F., Zhang Y.Y., Zweifel B.S., Seibert K. J. Med. Chem. 43:2000;775.
15. Sorbera L.A., Castaner R.M., Silvestre J., Castaner J. Drugs Fut. 26:2001;346.
16. Vainio H. Int. J. Cancer. 94:2001;613.
17. Kalgutkar A.S., Zhao Z. Curr. Drug. Targets. 2:2001;79.
18. Pasinetti G.M. J. Neurosci. Res. 54:1998;1.
19. Mukherjee D., Nissen S.E., Topol E.J. J. Am. Med. Assoc. 286:2001;954.
20. Chandrasekharan N.V., Dai H., Roos K.L., Evanson N.K., Tomsik J., Elton T.S., Simmons D.L. Proc. Natl. Acad. Sci. U.S.A. 99:2002;13371.
21. Xavier R. Drugs Today. 32:1996;365.
22. Cignarella G., Vianello P., Berti F., Rossoni G. Eur. J. Med. Chem. 31:1996;359.
23. Garcia-Nieto R., Perez C., Checa A., Gago F. Rheumatology. 38:1999;14.
24. Kurumbail R.G., Stevens A.M., Gierse J.K., McDonald J.J., Stegeman R.A., Pak J.Y., Gildehaus D., Miyashiro J.M., Penning T.D., Seibert K., Isakson P.C., Stallings W.C. Nature. 384:1996;644.
25. Pinto D.J.P., Batt D.G., Pitts W.J., Petraitis J.J., Orwat M.J., Wang S., Jetter J.W., Sherk S.R., Houghton G.C., Copeland R.A., Covington M.B., Trzaskos J.M., Magolda R.L. Bioorg. Med. Chem. Lett. 9:1999;919.
26. Li J.J., Norton M.B., Reinhard E.J., Anderson G.D., Gregory S.A., Isakson P.C., Koboldt C.M., Masferrer J.L., Perkins W.E., Seibert K., Zhang Y., Zweifel B.S., Reitz D.B. J. Med. Chem. 39:1996;1846.
27. Joo Y.H., Kim J.K., Kang S.H., Noh M.S., Ha J.Y., Chio J.K., Lim K.M., Lee C.H., Chung S. Bioorg. Med. Chem. Lett. 13:2003;413.
28. Praveen R.P.N., Amini M., Li H., Habeeb G., Knaus E.E. Bioorg. Med. Chem. Lett. 13:2003;2205.
29. Li C.S., Brideau C., Chan C.C., Savoie C., Claveau D., Charleson S., Gordon R., Greig G., Gauthier J.Y., Lau C.K., Riendeau D., Therien M., Wong E., Prasit P. Bioorg. Med. Chem. Lett. 13:2003;597.
30. Singh S.K., Reddy P.G., Rao K.S., Lohray B.B., Misra P., Rajjak S.A., Rao Y.K., Venkateswarlu A. Bioorg. Med. Chem. Lett. 14:2004;499.
31. Chan C.C., Boyce S., Brideau C., Charleson S., Cromlish W., Ethier D., Evans J., Ford-Hutchinson A.W., Forrest M.J., Gauthier J.Y., Gordon R., Gresser M., Guay J., Kargman S., Kennedy B., Leblanc Y., Leger S., Mancini J., O'Neill G.P., Ouellet M., Patrick D., Percival M.D., Perrier H., Prasit P., Rodger I., Tagari P., Therien M., Vickers P., Visco D., Wang Z., Webb J., Wong E., Xu L.J., Young R.N., Zamboni R., Riendeau D. J. Pharmacol. Exp. Ther. 290:1999;551.
32. Winter C.A., Risley E.A., Nuss G.W. Proc. Soc. Exp. Biol. Med. 111:1962;544.
33. Unpublished results.
34. All calculations were performed on Sybyl6.9 Octane 2 workstation. Molecules were sketched and minimized using MMFF94 force field and charges. Docking study was carried out using SC-558 bound 6COX (monomer) crystal structure with FlexX module of Sybyl. The active site was defined as 6.5 Å around the ligand. After docking, the ligands were merged in the binding site of COX-2, and energy minimization of this complex was performed using above method.