From indomethacin to a selective COX-2 inhibitor: Development of indolalkanoic acids as potent and selective cyclooxygenase-2 inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 6, 1996, Pages 725-730

  Black, W C ^a   Bayly, C ^a   Belley, M ^a   Chan, C C ^a   Charleson, S ^a   Denis, D ^a   Gauthier, J Y ^a   Gordon, R ^a   Guay, D ^a   Kargman, S ^a   Lau, C K ^a   Leblanc, Y ^a   Mancini, J ^a   Ouellet, M ^a   Percival, D ^a   Roy, P ^a   Skorey, K ^a   Tagari, P ^a   Vickers, P ^a   Wong, E ^a   Xu, L ^a   Prasit, P ^a   more..

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; INDOMETACIN; L 748780; L 761000; NONSTEROID ANTIINFLAMMATORY AGENT; PROSTAGLANDIN SYNTHASE; PROSTAGLANDIN SYNTHASE INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG SPECIFICITY; DRUG SYNTHESIS; ENZYME INHIBITION; GASTROINTESTINAL TOXICITY; NONHUMAN; ORAL DRUG ADMINISTRATION; RAT; STRUCTURE ACTIVITY RELATION;

EID: 0029981646     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00100-X     Document Type: Article

References (26)

1. (a) Hla, T.; Neilson, K. Proc. Natl. Acad. Sci. USA 1992, 89, 7384.
2. (b) Holtzman, M. J.; Turk, J.; Shornick, L. P. J. Biol. Chem. 1992, 267, 21438.
3. (c) Herschman, H. R. Cancer and Metastasis Reviews 1994, 13, 241.
4. (a) Kennedy, B. P.; Chan, C.-C.; Culp, S. A.; Cromlish, W. A. Biochem. Biophys. Res. Commun. 1993, 197, 494.
5. (b) Masferrer, J. L.; Zweifel, B. S.; Manning, P. T.; Hauser, S. D.; Leahy, K. M.; Smith, W. G.; Isakson, P. C.; Seibert, K. Proc. Natl. Acad. Sci. U.S.A 1994, 91, 3228.
6. (c) Vane, J. R.; Mitchell, J. A.; Appleton, I.; Tomlinson, A.; Bishop-Bailey, D.; Croxtall, J.; Willoughby, D. A. Proc. Natl. Acad. Sci. U.S.A 1994, 91, 2046.
7. (d) Harada, Y.; Hatanaka, K.; Saito, M.; Majima, M; Ogino, M.; Kawamura, M.; Ohno, T.; Yang, Q.; Katori, M.; Yamamoto, S. Biomed. Res. 1994, 15, 127.
8. (a) Mitchell, J. A.; Akarasereenont, P.; Thiemermann, C.; Flower, R. J.; Vane, J. R. Proc. Natl. Acad. Sci. U.S.A 1993, 90, 11693.
9. (b) Meade, E. A.; Smith, W. L.; DeWitt, D. L. J. Biol. Chem. 1993, 268, 6610.
10. Gans, K. R.; Galbraith, W.; Roman, R. J.; Haber, S. B.; Kerr, J. S.; Schmidt, W. K.; Smith, C.; Hewes, W. E.; Ackerman, N. R. J. Pharmacol. Exp. Ther. 1990, 254, 180.
11. Futaki, N.; Takahashi, S.; Yokoyama, M.; Arai, I.; Higuchi, S.; Otomo, S. Prostaglandins 1994, 47, 55.
12. Wiesenberg-Böttcher, I.; Schweizer, A.; Green, J. R.; Seltenmeyer, Y.; Müller, K. Agents Actions 1989, 26, 240.
13. (a) Prasit, P;. Black, W. C.; Chan, C.-C.; Ford-Hutchinson, A. W.; Gauthier, J. Y.; Gordon, R.; Guay, D.; Kargman, S.; Lau, C. K; Li, C.-S;. Mancini, J.; Ouimet, N.; Roy, P.; Targari, P.; Vickers, P.; Wong, E.; Young, R. N.; Zamboni R. Med. Chem. Res. 1995, 5, 364.
14. (b) Reitz, D. B.; Li, J. J.; Norton, M. B.; Reinhard, E. J.; Collins, J. T.; Andersen, G. D.; Gregory, S. A.; Koboldt, C. M.; Perkins, W. E.; Seibert, K.; Isakson, P. C. J. Med. Chem., 1994, 37, 3878.
15. (c) Reitz, D. B.; Huang, H.-C.; Li, J. J.; Garland, D. J.; Manning, R. E.; Anderson, G. D.; Gregory, S. A.; Koboldt, C. M.; Perkins, W. E.; Seibert, K.; Isakson, P. C. Bioorg. Med. Chem. Lett., 1995, 5, 867.
16. (d) Li, C.-S; .Black, W. 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.; Targari, P.; Vickers, P.; Wong, E.; Young, R. N.; Zamboni R.; Prasit, P. J. Med. Chem. 1995, 38, 4897.
17. (e) Leblanc Y.; Gauthier, J. Y.; Ethier, D.; Guay, J.; Mancini, J.; Riendeau, D.; Tagari, P.; Vickers, P.; Wong, E.; Prasit. P. Bioorg. Med. Chem. Lett., 1995, 5, 2123.
18. For a leading reference, see: Shen, T.-Y., Winter, C. A. Chemical and Biological Studies on Indomethacin, Sulindac and their Analogs. In Advances in Drug Research, Vol 12. Harper, N. J. and Simmonds, A. B., Eds; Academic Press: London, 1977; pp. 89-245.
19. Following paper in this journal.
20. All whole cell data is the average of at least two determinations performed in triplicate. Rat paw edema data is the average of at least 5 animals.
21. Chan, C.-C.; Boyce, S.; Brideau, C.; Ford-Hutchinson, A. W.; Gordon, R.; Guay, D.; Hill, R. G.; Li, C.-S.; Mancini, J.; Penneton, M.; Prasit, P.; Rasori, R.; Riendeau, D.; Roy, P.; Tagari, P.; Vickers, P.; Wong, E.; Rodger, I. W. J. Pharmacol. Exp. Ther. 1995, 274, 1531.
22. (a) Mancini, J. A.; O'Neill, G. P.; Bayly, C.; Vickers, P. J. FEBS Lett. 1994, 342, 33.
23. (b) Lecomte, M.; Laneeuville, O.; Ji, C.; DeWitt, D. L.; Smith, W. L. J. Biol. Chem. 1994, 269, 13207.
24. Funk, C. D.; Funk, L. B.; Kennedy, M. E.; Pong, A. S.; Fitzgerald, G. A. FASEB J. 1991, 5, 2304.
25. Structures were generated by energy minimization using the MMFF force field (Halgren, T. J. Comput. Chem., 1996, in press) and based on the X-ray crystal structure of indomethacin: Kistenmacher, T. J.; Marsh, R. E. J. Am. Chem. Soc., 1972, 94, 1340.
26. Structures were generated by energy minimization using the MMFF force field (Halgren, T. J. Comput. Chem., 1996, in press) and based on the X-ray crystal structure of indomethacin: Kistenmacher, T. J.; Marsh, R. E. J. Am. Chem. Soc., 1972, 94, 1340.