Synthesis and biological evaluation of new 4-carboxyl quinoline derivatives as cyclooxygenase-2 inhibitors

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 14, 2009, Pages 5312-5317

  Zarghi, Afshin ^a   Ghodsi, Razieh ^a   Azizi, Ebrahim ^b   Daraie, Bahram ^c   Hedayati, Mehdi ^a   Dadrass, Orkideh G ^d  

^a SHAHID BEHESHTI UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^b TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^c TARBIAT MODARES UNIVERSITY   (Iran)

^d ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

4 Carboxyl quinolines; Cyclooxygenase 2 inhibition; SAR

Indexed keywords

4 CARBOXYLQUINOLINE DERIVATIVE; 7,8,9,10 TETRAHYDRO 2 [4 (METHYLSULFONYL)PHENYL]BENZO[H]QUINOLINE 4 CARBOXYLIC ACID; CELECOXIB; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; IBUPROFEN; NAPROXEN; ROFECOXIB; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CRYSTAL STRUCTURE; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; IN VITRO STUDY; LIPOPHILICITY; MOLECULAR MODEL; PHARMACOPHORE; STRUCTURE ACTIVITY RELATION;

ANIMALS; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MURINAE; PROTEIN BINDING; QUINOLINES; SHEEP; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 67650083504     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.05.084     Document Type: Article

References (25)

1. Vane J.R. Nat. New Biol. 231 (1971) 232
2. Vane J.R., and Botting R.M. Inflamm. Res. 47 (1998) S78
3. Perini R., Fiorucci R., and Wallace J.L. Can. J. Gastroenterol. 18 (2004) 229
4. Vane J.R., Bakhle Y.S., and Botting R.M. Ann. Rev. Pharmacol. Toxicol. 38 (1998) 9704
5. Radi Z.A., and Khan N.K. Exp. Toxicol. Pathol. 58 (2006) 163
6. Aparicio Gallego G., Diaz Prado S., Jimenez Fonceca P., Garcia Campelo R., Cassinello Epinosa J., and Anton Aparicio L.M. Clin. Trans. Oncol. 9 (2007) 3305
7. Van Gool W.A., Aisen P.S., and Eikelenboom P. J. Neurol. 250 (2003) 788
8. Aisen P.S., Schafer K.A., Grundman M., Pfeiffer E., Sano M., Davis K.I., Farlow M.R., Jin S., Thomas R.G., and Thal L.J. JAMA 289 (2003) 2819
9. Penning T.D., Tally J.J., Bertenshaw S.R., Carter J.S., Collins P.W., Doctor 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., and Isakson P.C. J. Med. Chem. 40 (1997) 1347
10. 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., Leger S., Mancini J., O'Neill G.P., Quellet M., Percival M.D., Perrier H., Riendeau D., Rodger I., Tagari P., Therien M., Vickers P., Wong E., Xu L.J., Young R.N., Zamboni R., Boyce S., Rupniak N., Forrest M., Visco D., and Patrick D. Bioorg. Med. Chem. Lett. 9 (1999) 1773
11. Dannhardt G., and Kiefer W. Eur. J. Med. Chem. 36 (2001) 109
12. Dogné J.M., Supuran C.T., and Pratico D. J. Med. Chem. 48 (2005) 2251
13. Solomon D.H. Arthritis Rheum. 52 (2005) 1968
14. Mason R.P., Walter M.F., McNulty H.P., Lockwood S.F., Byun J., Day C.A., and Jacob R.F. J. Cardivasc. Pharmacol. 47 (2006) S7
15. Zarghi A., Tahghighi A., Soleimani Z., Daraei B., Dadrass O.G., and Hedayati M. Sci. Pharm. 76 (2008) 361
16. Llorens O., Perez J.J., Palomer A., and Mauleon D. J. Mol. Graphics Modell. 20 (2002) 359
17. Atwell G.J., Baguley B.C., and Denny W.A. J. Med. Chem. 32 (1989) 396
18. Zarghi A., Arfaee S., Rao P.N.P., and Knaus E.E. Bioorg. Med. Chem. 14 (2006) 2600
19. Anreichikov Y.S., Gein V.L., and Anikina I.N. Zh. Org. Khim. 24 (1988) 875
20. Mueller G.P., and Stobaugh R.E. J. Am. Chem. Soc. 72 (1950) 1598
21. Therien M., Gauthier J.Y., Leblanc Y., Leger S., Perrier H., Prasit P., and Wang Z. Synthesis 12 (2001) 1778
22. Garavito R.M., and DeWitt D.L. Biochim. Biophys. Acta 1441 (1999) 278
23. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., and Olson A. J. Comput. Chem. 19 (1998) 1639
24. Kurumbail R.G., Stevens A.M., Gierse J.K., McDonald J.J., Stegeman R.A., Pak J.Y., Gildehaus D., Miyashiro J.M., Penning T.D., Seibert K., Isakson P.C., and Stallings W.C. Nature 384 (1996) 644
25. Zarghi A., Najafnia L., Daraee B., Dadrass O.G., and Hedayati M. Bioorg. Med. Chem. Lett. 17 (2007) 5634