Computational studies of COX-2 inhibitors: 3D-QSAR and docking

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 7, 2004, Pages 1629-1641

  Kim, Hye Jung ^a,b   Chae, Chong Hak ^a   Yi, Kyu Yang ^a   Park, Kyung Lae ^b   Yoo, Sung Eun ^a  

^a Korea Research Institute of Chemical Technology   (South Korea)

^b Chungnam National University   (South Korea)

Author keywords

3D QSAR; COMBINE; CoMFA; CoMSIA; COX 2; Docking

Indexed keywords

CYCLOOXYGENASE 2 INHIBITOR;

ARTICLE; BINDING AFFINITY; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; CORRELATION ANALYSIS; ELECTRICITY; MATHEMATICAL COMPUTING; QUANTITATIVE STRUCTURE ACTIVITY RELATION; REGRESSION ANALYSIS; STATISTICAL MODEL; STATISTICAL SIGNIFICANCE;

BINDING SITES; COMPUTATIONAL BIOLOGY; COMPUTER SIMULATION; CYCLOOXYGENASE INHIBITORS; DRUG DESIGN; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN BINDING; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; REPRODUCIBILITY OF RESULTS;

EID: 1542613792     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.01.027     Document Type: Article

References (54)

1. Vane J.R., Botting R.M. Scand. J. Rheumatol. Suppl. 102:1996;9.
2. Dannhardt G., Kiefer W. Eur. J. Med. Chem. 36:2001;109.
3. Fu J.Y., Masferrer J.L., Seibert K., Raz A., Needleman P. J. Biol. Chem. 265:1990;16737.
4. Crofford L.J. J. Rheumatol. 24(Suppl 49):1997;15.
5. Marnett L.J. Curr. Opin. Chem. Biol. 4:2000;545.
6. Laneuville O., Breuer D.K., Dewitt D.L., Hla T., Funk C.D., Smith W.L. J. Pharmacol. Exp. Ther. 271:1994;927.
7. Marnett L.J., Kalgutkar A.S. Curr. Opin. Chem. Biol. 2:1998;482.
8. 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.
9. Prasit P., Wang Z., Brideau C., Chan C.C., Charleson S., Cromlish W., Ethier D., Evans J.F., Ford-Hutchinson A.W., Gauthier J.Y., Gordon R., Guay J., Gresser M., Kargman S., Kennedy B., Leblanc Y., Léger S., Mancini J., O'Neill G.P., Ouellet M., Percival M.D., Perrier H., Riendeau D., Rodger I., Tagari P., Thérien M., Vickers P., Wong E., Xu L.-J., Young R.N., Zamboni R. Bioorg. Med. Chem. Lett. 9:1999;1773.
10. 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.
11. Riendeau D., Percival M.D., Brideau C., Charleson S., Dube D., Ethier D., Falgueyret J.P., Friesen R.W., Gordon R., Greig G., Guay J., Mancini J., Ouellet M., Wong E., Xu L., Boyce S., Visco D., Girard Y., Prasit P., Zamboni R., Rodger I.W., Gresser M., Ford-Hutchinson A.W., Young R.N., Chan C.C. J. Pharmacol. Exp. Ther. 296:2001;558.
12. Vane J.R., Botting R.M. Inflamm. Res. 47(Suppl 2):1998;S78.
13. Talley J.J., Bertenshaw S.R., Brown D.L., Carter J.S., Graneto M.J., Kellogg M.S., Koboldt C.M., Yuan J., Zhang Y.Y., Seibert K. J. Med. Chem. 43:2000;1661.
14. Sawdy R., Slater D., Fisk N., Edmonds D.K., Bennett P. Lancet. 350:1997;265.
15. Kutchera W., Jones D.A., Matsunami N., Groden J., McIntyre T.M., Zimmerman G.A., White R.L., Prescott S.M. Proc. Natl. Acad. Sci. U.S.A. 93:1996;4816.
16. Stewart W.F., Kawas C., Corrada M., Metter E.J. Neurology. 48:1997;626.
17. Subbaramaiah K., Dannenberg A.J. Trends Pharmacol. Sci. 24:2003;96.
18. Gierse J.K., Koboldt C.M., Walker M.C., Seibert K., Isakson P.C. Biochem. J. 339:1999;607.
19. Walker M.C., Kurumbail R.G., Kiefer J.R., Moreland K.T., Koboldt C.M., Isakson P.C., Seibert K., Gierse J.K. Biochem. J. 357:2001;709.
20. Bosch J., Roca T., Catena J.L., Llorens O., Perez J.-J., Lagunas C., Fernández A.G., Miquel I., Fernández-Serrat A., Farrerons C. Bioorg. Med. Chem. Lett. 10:2000;1745.
21. Habeeb A.G., Praveen Rao P.N., Knaus E.E. Drug. Des. Res. 51:2000;273.
22. Habeeb A.G., Praveen Rao P.N., Knaus E.E. J. Med. Chem. 44:2001;2921.
23. Almansa C., Alfon J., De Arriba A.F., Cavalcanti F.L., Escamilla I., Gomez L.A., Miralles A., Soliva R., Bartroli J., Carceller E., Merlos M., Garcia-Rafanell J. J. Med. Chem. 46:2003;3463.
24. Marot C., Chavatte P., Lesieur D. Quant. Struct.-Act. Relat. 19:2000;127.
25. Desiraju G.R., Gopalakrishnan B., Jetti R.K.R., Raveendra D., Sarma J.A.R.P.et al. Molecules. 5:2000;945.
26. Desiraju G.R., Sarma J.A.R.P., Raveendra D., Gopalakrishnan B., Thilagavathi R.et al. J. Phys. Org. Chem. 14:2001;481.
27. Desiraju G.R., Gopalakrishnan B., Jetti R.K., Nagaraju A., Raveendra D., Sarma J.A., Sobhia M.E., Thilagavathi R. J. Med. Chem. 45:2002;4847.
28. Liu H., Huang X., Shen J., Luo X., Li M., Xiong B., Chen G., Shen J., Yang Y., Jiang H., Chen K. J. Med. Chem. 45:2002;4816.
29. Chavatte P., Yous S., Marot C., Baurin N., Lesieur D. J. Med. Chem. 44:2001;3223.
30. Plount Price M.L., Jorgensen W.L. J. Am. Chem. Soc. 122:2000;9455.
31. Soliva R., Almansa C., Kalko S.G., Luque F.J., Orozco M. J. Med. Chem. 46:2003;1372.
32. Pouplana R., Lozano J.J., Perez C., Ruiz J. J. Comput. Aided. Mol. Des. 16:2002;683.
33. Wong E., Bayly C., Waterman H.L., Riendeau D., Mancini J.A. J. Biol. Chem. 272:1997;9280.
34. 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.
35. Portevin B., Tordjman C., Pastoureau P., Bonnet J., De Nanteuil G. J. Med. Chem. 43:2000;4582.
36. Sui Z., Guan J., Ferro M.P., McCoy K., Wachter M.P., Murray W.V., Singer M., Steber M., Ritchie D.M., Argentieri D.C. Bioorg. Med. Chem. Lett. 10:2000;601.
37. Chakraborti A.K., Thilagavathi R. Bioorg. Med. Chem. 11:2003;3989.
38. Cramer R.D., Patterson D.E., Bunce J.D. J. Am. Chem. Soc. 110:1988;5959.
39. Klebe G., Abraham U., Mietzner T. J. Med. Chem. 37:1994;4130.
40. Brooks B.R., Bruccoleri R.E., Olafson B.D., States D.J., Swaminathan S. et al. J. Comput. Chem. 4:1983;187.
41. York D. Canada. J. Phys. 44:1966;1079.
42. Ortiz A.R., Pisabarro M.T., Gago F., Wade R.C. J. Med. Chem. 38:1995;2681.
43. Hashimoto H., Imamura K., Haruta J., Wakitani K. J. Med. Chem. 45:2002;1511.
44. Hashimoto H., Maeda K., Ozawa K., Haruta J., Wakitani K. Bioorg. Med. Chem. Lett. 12:2002;65.
45. Lau C.K., Brideau C., Chan C.C., Charleson S., Cromlish W.A., Ethier D., Gauthier J.Y., Gordon R., Guay J., Kargman S., Li C.-S., Prasit P., Riendeau D., Thérien M., Visco D.M., Xu L. Bioorg. Med. Chem. Lett. 9:1999;3187.
46. Friesen R.W., Dube 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.
47. Huang H.C., Chamberlain T.S., Selbert K., Koboldt C.M., Isakson P.C., Reitz D.B. Bioorg. Med. Chem. Lett. 5:1995;2377.
48. Bertenshaw S.R., Talley J.J., Rogier D.J., Graneto M.J., Koboldt C.M., Yan Z. Bioorg. Med. Chem. Lett. 6:1996;2827.
49. Therien M., 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., O'Neill G.P., Reindeau D., Roy P., Wang Z., Xu L., Prasit P. Bioorg. Med. Chem. Lett. 7:1997;47.
50. van der Voet H. Chemometrics and Intelligent Laboratory Systems. 25:1994;313.
51. Tripos Associates, I. 1699, MO 63144.
52. Gasteiger H., Marsili M. Tetrahedron. 36:1980;3219.
53. Kurumbail R.G., Stevens A.M., Gierse J.K., McDonald J.J., Stegeman R.A. et al. Nature. 384:1996;644.
54. Norinder U., Rivera C., Unden A. J. Pept. Res. 49:1997;155.