Discovery of 2-phenyl-3-sulfonylphenyl-indole derivatives as a new class of selective COX-2 inhibitors

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 24, 2003, Pages 5539-5544

  Hu, Wenhui ^a   Guo, Zongru ^a   Yi, Xiang ^a   Guo, Changbin ^a   Chu, Fengming ^a   Cheng, Guifang ^a  

^a INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 (2 ACETYLOXYPHENYL) 3 (4 METHYLSULFONYLPHENYL) 5 CHLOROINDOLE; 2 (2 FLUOROPHENYL) 3 (4 METHYLSULFONYLPHENYL) 5 CHLOROINDOLE; 2 (4 ACETYLOXYPHENYL) 3 (4 METHYLSULFONYLPHENYL) 5 CHLOROINDOLE; 2 (4 CHLOROPHENYL) 3 (4 METHYLSULFONYLPHENYL) 5 CHLOROINDOLE; 2 (4 METHOXYPHENYL) 3 (4 METHYLSULFONYLPHENYL) 5 CHLOROINDOLE; 2 (4 METHYLPHENYL) 3 (4 METHYLSULFONYLPHENYL) 5 CHLOROINDOLE; 2 (4 METHYLSUFONYLPHENYL) 3 (4 METHYLSULFONYLPHENYL) 5 CHLOROINDOLE; 2 (4 METHYLSULFONYLPHENYL) 3 (4 METHYLSULFONYLPHENYL) 5 METHYLINDOLE; 2 PHENYL 3 (4 AMINOSULFONYLPHENYL)INDOLE; 2 PHENYL 3 (4 METHYLSULFONYLPHENYL) 5 CHLOROINDOLE; 2 PHENYL 3 (4 METHYLSULFONYLPHENYL)INDOLE; CELECOXIB; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; ASSAY; CELL VIABILITY; CONTROLLED STUDY; DRUG IDENTIFICATION; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; IC 50; MALE; MOUSE; NONHUMAN; PERITONEUM CELL;

EID: 0345282989     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2003.09.008     Document Type: Article

References (46)

1. Vane J.R. Nature. 231:1971;232.
2. Allison M.C., Howatson A.G., Torrance C.J., Lee F.D., Russell R.I. N. Engl. J. Med. 327:1992;749.
3. O'Banion M.K., Sadowski H.B., Winn V., Young D.A. J. Biol. Chem. 266:1991;23261.
4. Kujubu D.A., Herschmann H.R. J. Biol. Chem. 267:1992;7991.
5. De Brum-Fernandez A.J. J. Rheumatol. 24:1997;246.
6. 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.W., Zhang Y.Y., Isakson P.C. J. Med. Chem. 40:1997;1347.
7. Prasit P., Wang Z., Brideau C., Chan C.C., Charleson S., Cromlish W., Ethier D., Evans J.F. Bioorg. Med. Chem. Lett. 9:1999;1773.
8. Nicoll Griffith D.A., Yergey J.A., Trimble L.A., Silva J.M., Li C., Chauret N., Gauthier J.Y., Grimm E., Leger S., Roy P., Therien M., Wang Z.Y., Prasit P., Zamboni R., Young R.N., Brideau C., Chan C.-C., Mancini J., Riendeau D. Bioorg. Med. Chem. Lett. 10:2000;2683.
9. 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.
10. Friesen R.W., Dubé D., Fortin R., Frenette R., Prescott S., Cromlish W., Greig G.M., Kargman S., Wong E., Chan C.C., Gordon R., Xu L., Riendeau D. Bioorg. Med. Chem. Lett. 6:1996;2677.
11. Reitz D.B., Li J.J., Norton M.B., Reinhart E.J., Collins J.T., Anderson G.D., Gregory S.A., Koboldt C.M., Perkins W.E., Seibert K., Isakson P.C. J. Med. Chem. 37:1994;3878.
12. Li J.J., Anderson G.D., Burton E.G., Cogburn J.N., Collins J.T., Garland D.J., Gregory S.A., Huang H.C., Isakson P.C., Koboldt C.M., Logusch E.W., Norton M.B., Perkins W.E., Reinhard E.J., Seibert K., Veenhuizen A.W., Zhang Y., Reitz D.B. J. Med. Chem. 38:1995;4570.
13. Black W.C., Brideau C., Chan C.C., Charleson S., Chauret N., Claveau D., Ethier D., Gordon R., Greig G., Guay J., Hughes G., Jolicoeur P., Leblanc Y., Nicoll-Griffith D., Ouimet N., Riendeau D., Visco D., Wang Z., Xu L., Prasit P. J. Med. Chem. 42:1999;1274.
14. Huang H.C., Li J.J., Garland D.J., Chamberlain T.S., Reinhard E.J., Manning R.E., Seibert K., Koboldt C.M., Gregory S.A., Anderson G.D., Veenhuizen A.W., Zhang Y., Perkins W.E., Burton E.G., Cogburn J.N., Isakson P.C., Reitz D.B. J. Med. Chem. 39:1996;253.
15. Palomer A., Cabre F., Pascual J., Campos J., Trujillo M.A., Entrena A., Gallo M.A., Garcia L., Mauleon D., Espinosa A. J. Med. Chem. 45:2002;1402.
16. 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. 5:1995;2123.
17. Gauthier J.Y., Leblanc Y., Black W.C., Chan C.C., Cromlish W.A., Gordon R., Kennedey B.P., Lau P.K., Leger S., Wang Z., Ethier D., Guay J., Mancini J., Riendeau D., Tagari P., Vickers P., Wong E., Xu L., Prasit P. Bioorg. Med. Chem. Lett. 6:1996;87.
18. Khanna I.K., Weier R.M., Yu Y., Collins P.W., Miyashiro J.M., Koboldt C.M., Veenhuizen A.W., Currie J.L., Seibert K., Isakson P.C. J. Med. Chem. 40:1997;1619.
19. Leblanc Y., Roy P., Boyce S., Brideau C., Chan C.C., Charleson S., Gordon R., Grimm E., Guay J., Leger S., Li C.S., Riendeau D., Visco D., Wang Z., Webb J., Xu L., Prasit P. Bioorg. Med. Chem. Lett. 9:1999;2207.
20. Lau C.K., Brideau C., Chan C.C., Charleson S., Cromlish W., Ethier D., Gauthier J.Y., Gordon R., Guay J., Kargman S., Li C.S., Prasit P., Riendeau D., Therien M., Visco D., Xu L. Bioorg. Med. Chem. Lett. 9:1999;3187.
21. Shin S.S., Noh M.S., Byun Y.J., Choi J.K., Kim J.Y., Lim K.M., Ha J.Y., Kim J.K., Lee C.H., Chung S. Bioorg. Med. Chem. Lett. 11:2001;165.
22. Bai A.P., Guo Z.R., Hu W.H., Shen F., Cheng G.F. Chin. Chem. Lett. 12(9):2001;775.
23. Khanna I.K., Weier R.M., Yu Y., Xu X.D., Koszyk F.J., Collins P.W., Koboldt C.M., Veenhuizen A.W., Perkins W.E., Casler J.J., Masferrer J.L., Zhang Y.Y., Gregory S.A., Seibert K., Isakson P.C. J. Med. Chem. 40:1997;1634.
24. Khanna I.K., Yu Y., Huff R.M., Weier R.M., Xu X., Koszyk F.J., Collins P.W., Cogburn J.N., Isakson P.C., Koboldt C.M., Masferrer J.L., Perkins W.E., Seibert K., Veenhuizen A.W., Yuan J., Yang D.C., Zhang Y.Y. J. Med. Chem. 43:2000;3168.
25. Hashimoto H., Imamura K., Haruta J., Wakitani K. J. Med. Chem. 45:2002;1511.
26. Puig C., Crespo M.I., Godessart N., Feixas J., Ibarzo J., Jimenez J.-M., Soca L., Cardelus I., Heredia A., Miralpeix M., Puig J., Beleta J., Huerta J.M., Lopez M., Segarra V., Ryder H., Palacios J.M. J. Med. Chem. 43:2000;214.
27. 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.
28. Friesen R.W., Brideau C., Chan C.C., Charleson S., Deschenes D., Dubé D., Ethier D., Fortin R., Gauthier J.Y., Girard Y., Gordon R., Greig G.M., Riendeau D., Savoie C., Wang Z., Wong E., Visco D., Xu L., Young R.N. Bioorg. Med. Chem. Lett. 8:1998;2777.
29. Dubé D., Brideau C., Deschênes D., Fortin R., Friesen R.W., Gordon R., Girard Y., Riendeau D., Savoie C., Chan C.C. Bioorg. Med. Chem. Lett. 9:1999;1715.
30. Almansa C., de Arriba A.F., Cavalcanti F.L., Gomez L.A., Miralles A., Merlos M., Garcia-Rafanell J., Forn J. J. Med. Chem. 44:2001;350.
31. Michel T., Brideau C., Chan C.C., Cromlish W.A., Gauthier J.Y., Gordon R., Greig G., Kargman S., Lau C.K., Leblanc Y., Li C.S., Oneill G.P., Riendeau D., Roy P., Wang Z., Xu L., Prasit P. Bioorg. Med. Chem. Lett. 7:1997;47.
32. Roy P., Leblanc Y., Ball R.G., Brideau C., Chan C.C., Chauret N., Cromlish W., Ethier D., Gauthier J.Y., Gordon R., Greig G., Guay J., Kargman S., Lau C.K., Oneill G.P., Silva J., Therien M., van Staden M., Wong E., Xu L., Prasit P. Bioorg. Med. Chem. Lett. 7:1997;57.
33. Laval X., Delarge J., Somers F., Tullio P., Henrotin Y., Pirotte B., Dogne J.M. Curr. Med. Chem. 7:2000;1041.
34. Dannhardt G., Kiefe W. Eur. J. Med. Chem. 36:2001;109.
35. Futaki N., Takahashi S., Yokoyama I., Arai I., Higuchi S., Otomo S. Prostaglandins. 47:1994;55.
36. 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., Vickers P., Wong E., Young R.N., Zamboni R., Prasit P. J. Med. Chem. 38:1995;4897.
37. Ouimet N., Chan C.C., Charleson S., Claveau D., Gordon R., Guay D., Li C.S., Ouellet M., Percival D., Riendeau D., Wong E., Zamboni R., Prasit P. Bioorg. Med. Chem. Lett. 9:1999;151.
38. Kalgutkar A.S., Crews B.C., Rowlinson S.W., Garner C., Seibert K., Lawrence J., Marnett L.J. Science. 280:1998;1268.
39. Kalgutkar A.S., Marnett A.B., Crews B.C., Remmel R.P., Marnett L.J. J. Med. Chem. 43:2000;2860.
40. Black W.C., Bayly C., Belley M., Chan C.C., Charleson S., Denis D., Gauthier J.Y., Gordon R., Guay D., Kargman S., Lau C.K., Leblanc Y., Mancini J., Ouellet M., Percival D., Roy P., Skorey K., Tagari P., Vickers P., Wong E., Xu L., Prasit P. Bioorg. Med. Chem. Lett. 6:1996;725.
41. Bayly C.I., Black W.C., Leger S., Ouimet N., Ouellet M., Percival D. Bioorg. Med. Chem. Lett. 9:1999;307.
42. Hu W.H., Guo Z.R., Chu F.M., Bai A.P., Yi X., Cheng G.F., Li J. Bioorg. Med. Chem. 11:2003;1153.
43. Fürstner A., Hupperts A., Ptock A., Janssen E. J. Org. Chem. 59:1994;5215.
44. Fürstner A., Hupperts A. J. Am. Chem. Soc. 117:1995;4468.
45. Fürstner A., Jumbam D.N. Tetrahedron. 48:1992;5991.
46. Hu Y.F., Cheng G.F. Acta Pharmaceutica Sinica. 35:2000;343.