Design, synthesis, and biological evaluation of N-acetyl-2-(or 3-)carboxymethylbenzenesulfonamides as cyclooxygenase isozyme inhibitors

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 15, 2005, Pages 4694-4703

  Chen, Qiao Hong ^a   Rao, P N Praveen ^a   Knaus, Edward E ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Anti inflammatory activity; Cyclooxygenase inhibition; N Acetyl 2 (or 3 )carboxymethylbenzenesulfonamides

Indexed keywords

ACETYLSALICYLIC ACID; ANALGESIC AGENT; ANTIINFLAMMATORY AGENT; BENZENESULFONAMIDE DERIVATIVE; CYCLOOXYGENASE 2 INHIBITOR; N ACETYL 2 CARBOXYMETHYL 4 (2,4 DIFLUOROPHENYL)BENZENESULFONAMIDE; N ACETYL 2 CARBOXYMETHYL 4 FLUOROBENZENESULFONAMIDE; N ACETYL 2 CARBOXYMETHYL 6 (4 ISOPROPOXYPHENYL)BENZENESULFONAMIDE; N ACETYL 3 CARBOXYMETHYL 6 (4 METHANESULFONYLPHENYL)BENZENESULFONAMIDE; N ACETYL 3 CARBOXYMETHYL 6 FLUOROBENZENESULFONAMIDE; PALLADIUM; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; CROSS COUPLING REACTION; DRUG ACTIVITY; DRUG DESIGN; DRUG INHIBITION; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; IN VITRO STUDY; NONHUMAN; PAW EDEMA; RAT; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SUZUKI REACTION;

ANIMALS; ANTI-INFLAMMATORY AGENTS; ASPIRIN; BINDING SITES; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; CYCLOOXYGENASE INHIBITORS; DRUG DESIGN; INHIBITORY CONCENTRATION 50; ISOENZYMES; MEMBRANE PROTEINS; MICE; MOLECULAR STRUCTURE; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 20544463415     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.04.069     Document Type: Article

References (22)

1. M. Hamberg, and B. Samuelsson J. Biol. Chem. 242 1967 5336
2. T. Miyamoto, N. Ogino, S. Yamamoto, and O. Hayaishi J. Biol. Chem. 251 1976 2629
3. B.S. Fletcher, D.A. Kujubu, D.M. Perrin, and H.R. Herschman J. Biol. Chem. 267 1992 4338
4. J.R. Vane, Y.S. Bakhle, and R.M. Botting Annu. Rev. Pharmacol. Toxicol. 38 1998 97
5. E.A. Meade, W.L. Smith, and D.L. DeWitt J. Biol. Chem. 268 1993 6610
6. F.E. Silverstein, G. Faich, J.L. Goldstein, L.S. Simon, T. Pincus, A. Whelton, R. Makuch, G. Eisen, N.M. Agrawal, W.F. Stenson, A.M. Burr, W.W. Zhao, J.D. Kent, J.B. Lefkowith, K.M. Verburg, and G.S. Geis J. Am. Med. Assoc. 284 2000 1247
7. C. Hawkey, L. Laine, T. Simon, A. Beaulieu, C.J. Maldonado, E. Acevedo, A. Shahane, H. Quan, J. Bolognese, and E. Mortensen Arthritis Rheum. 43 2000 370
8. D. Mukherjee, S.E. Nissen, and E.J. Topol J. Am. Med. Assoc. 286 2001 954 and references cited therein
9. A.S. Kalgutkar, B.C. Crews, S.W. Rowlinson, C. Garner, K. Seibert, and L.J. Marnett Science 280 1998 1268
10. A.S. Kalgutkar, K.R. Kozak, B.C. Crews, G.P. Hochgesang Jr., and L.J. Marnett J. Med. Chem. 41 1998 4800
11. G.P. Hochgesang Jr., J.F. Nemeth-Cawley, S.W. Rowlinson, R.M. Caprioli, and L. Marnett Arch. Biochem. Biophys. 409 2003 127
12. M.A. Rahim, P.N.P. Rao, and E.E. Knaus Bioorg. Med. Chem. Lett. 12 2002 2753
13. N.O. Sykes, S.J.F. Macdonald, and M.I. Page J. Med. Chem. 45 2002 2850
14. A. Zarghi, P.N.P. Rao, and E.E. Knaus Bioorg. Med. Chem. Lett. 14 2004 1975
15. Q.H. Chen, P.N.P. Rao, and E.E. Knaus Bioorg. Med. Chem. 13 2005 2459
16. N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457
17. S.P. Stanforth Tetrahedron 54 1998 263
18. E. Sianesi, R. Redaelli, M. Bertani, and P. Da Re Chem. Ber. 103 1970 1992
19. C.I. Bayly, W.C. Black, S. Leger, N. Ouimet, M. Ouellet, and M.D. Percival Bioorg. Med. Chem. Lett. 9 1996 307
20. M.J. Uddin, P.N.P. Rao, and E.E. Knaus Bioorg. Med. Chem. 12 2004 5929
21. C.A. Winter, E.A. Risley, and G.W. Nuss Proc. Soc. Exp. Biol. Med. 111 1962 544
22. K. Fukawa, O. Kawano, M. Hibi, N. Misaka, S. Ohba, and Y. Hatanaka J. Pharmacol. Methods 4 1980 251