Substituted heterocyclic analogs as selective COX-2 inhibitors in the flosulide class

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 2, 1999, Pages 151-156

  Ouimet, Nathalie ^a   Chan, Chi Chung ^a   Charleson, Stella ^a   Claveau, David ^a   Gordon, Robert ^a   Guay, Daniel ^a   Chun Sing, Li ^a   Ouellet, Marc ^a   Percival, David M ^a   Riendeau, Denis ^a   Wong, Elizabeth ^a   Zamboni, Robert ^a   Prasit, Petpiboon ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

6 (2,4 DIFLUOROPHENYLTHIO) 5 METHANESULFONAMIDO 1 INDANONE; ANTIINFLAMMATORY AGENT; CYCLOOXYGENASE 2 INHIBITOR; FLOSULIDE;

ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; DRUG EFFICACY; DRUG POTENCY; DRUG STRUCTURE; ENZYME INHIBITION; NONHUMAN; PAIN; PAW EDEMA; PROSTAGLANDIN SYNTHESIS INHIBITION; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALS; CHO CELLS; CRICETINAE; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; CYCLOOXYGENASE INHIBITORS; HUMANS; INDANS; INHIBITORY CONCENTRATION 50; ISOENZYMES; MEMBRANE PROTEINS; MICROSOMES; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; SULFONAMIDES; U937 CELLS;

ANIMALIA;

EID: 0033579963     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00705-7     Document Type: Article

References (15)

1. Jouzeau, J.-Y.; Terlain, B.; Abid A.; Nédélec, E.; Netter, P. Drugs 1997, 563.
2. (b) Bakhle, Y. S.; Botting, R. M. Mediators of Inflammation 1996, 5, 305.
3. (c) Griswold, D. E.; Adams, L. Med. Res. Rev. 1996, 16, 181.
4. (d) Prasit, P.; Riendeau, D. Ann. Rep. in Med. Chem. 1997, 32, 211.
5. Mitchell, J. A.; Akarasereenont, P.; Thiermermann, C.; Flower, R. J.; Vane, J. R. Proc. Natl. Acad. Sci. U.S.A 1993, 90, 11693.
6. Klein, T.; Nusing, R. M.; Pfeilschifter, J.; Ullrich, V. Biochem. Pharmaco. 1994, 48, 1605.
7. Li, C-S; Black, C.; Chan, C-C.; Ford-Hutchinson, A. W.; Gauthier, J-Y; Gordon, R.; Guay, D.; Kargman, S.; Lau, C. K.; Mancini, J.; Ouimet, N.; Roy, P.; Vickers, P.; Wong, E.; Young, R. N.; Zamboni, R.; Prasit, P. J. Med. Chem. 1995, 38, 4897.
8. Tsuji, K.; Nakamura, K.; Konishi, N.; Okumura, H.; Matsuo, M. Chem. Pharm. Bull. 1992, 40, 2399.
9. Buchman, E. R.; Sargent, H. J. Am. Chem. Soc. 1945, 67, 400.
10. Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini P. Synthesis Stuttgart 1987, 998.
11. Young, R. N.; Gauthier, J.-Y.; Coombs, W. Tetrahedron Lett. 1984, 25, 1753.
12. Inhibition of purified recombinant human COX-1 and COX-2 was measured after 15 min pre-incubation of inhibitor with the enzyme prior to assay with the cosubstrate TMPD and 100 μM arachidonic acid in the presence of the detergent genapol X-100 (2 mM). See : Riendeau, D.; Percival, M. D.; Boyce, S.; Brideau, C.; Charleson, S.; Cromlish, W.; Ethier, D.; Evans, J.; Falgueyret, J.-P.; Ford-Hutchinson, A. W.; Gordon, R.; Greig, G.; Gresser, M.; Guay, J.; Kargman, S.; Léger, S.; Mancini, J. A.; O'Neill, G.; Ouellet, M.; Rogers. I. W.; Therien, M.; Wang, Z; Webb, J. K.; Wong, E.; Xu, L.; Young, R. N.; Zamboni, R.; Prasit, P.; Chan, C.-C. Brit. J. Pharmacol. 1997, 121, 105. Kargman, S.; Wong, E.; Greig, G. M.; Falgueret, J.-P.; Cromlish, W.; Ethier, D.; Yergey, J. A.; Riendeau, D.; Evans, J. F.; Kennedy, B.; Tagari, P.; Francis, D. A.; O'Neill, G. P. Biochem. Pharmaco. 1996, 52, 1113.
13. Inhibition of purified recombinant human COX-1 and COX-2 was measured after 15 min pre-incubation of inhibitor with the enzyme prior to assay with the cosubstrate TMPD and 100 μM arachidonic acid in the presence of the detergent genapol X-100 (2 mM). See : Riendeau, D.; Percival, M. D.; Boyce, S.; Brideau, C.; Charleson, S.; Cromlish, W.; Ethier, D.; Evans, J.; Falgueyret, J.-P.; Ford-Hutchinson, A. W.; Gordon, R.; Greig, G.; Gresser, M.; Guay, J.; Kargman, S.; Léger, S.; Mancini, J. A.; O'Neill, G.; Ouellet, M.; Rogers. I. W.; Therien, M.; Wang, Z; Webb, J. K.; Wong, E.; Xu, L.; Young, R. N.; Zamboni, R.; Prasit, P.; Chan, C.-C. Brit. J. Pharmacol. 1997, 121, 105. Kargman, S.; Wong, E.; Greig, G. M.; Falgueret, J.-P.; Cromlish, W.; Ethier, D.; Yergey, J. A.; Riendeau, D.; Evans, J. F.; Kennedy, B.; Tagari, P.; Francis, D. A.; O'Neill, G. P. Biochem. Pharmaco. 1996, 52, 1113.
14. Riendeau, D.; Charleson, S.; Cromlish, W.; Mancini, J. A.; Wong, E.; Guay, J. Can. J. Physiol. Pharmacol. 1997, 75, 1088.
15. Chan, C.-C.; Boyce, S.; Brideau, C; Ford-Hutchinson, A. W.; Gordon, R.; Guay, D.; Hill, R.; Li, C.-S.; Mancini, J.; Panneton, M.; Prasit, P.; Rasori, R.; Riendeau, D.; Roy, P.; Tagari, P.; Vickers, P.; Wong,; Rodgers, I. W. J. Pharmacol. Exp. Ther 1995, 274, 1531.