Design, synthesis and biological evaluation of new (E)- and (Z)-1,2,3-triaryl-2-propen-1-ones as selective COX-2 inhibitors

European Journal of Medicinal Chemistry

Volumn 45, Issue 9, 2010, Pages 4013-4017

  Arfaie, Sara ^a   Zarghi, Afshin ^a  

^a SHAHID BEHESHTI UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

1,2,3 Triaryl 2 propen 1 ones; Cyclooxygenase 2 inhibition; Selectivity; Synthesis

Indexed keywords

1 (4 (METHYLSULFONYL)PHENYL) 2 PHENYL 3 (THIOPHEN 2 YL)PROP 2 EN 1 ONE; 1 (4 (METHYLSULFONYL)PHENYL) 2 PHENYL 3 4 TOLYLPROP 2 EN 1 ONE; 1 (4 (METHYLSULFONYL)PHENYL) 2,3 DIPHENYLPROP 2 EN 1 ONE; 3 (4 FLUOROPHENYL) 1 (4 (METHYLSULFONYL)PHENYL) 2 PHENYLPROP 2 EN 1 ONE; 3 (4 HYDROXYPHENYL) 1 (4 (METHYLSULFONYL)PHENYL) 2 PHENYLPROP 2 EN 1 ONE; 3 (4 METHOXYPHENYL) 1 (4 (METHYLSULFONYL)PHENYL) 2 PHENYLPROP 2 EN 1 ONE; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION; IN VITRO STUDY; STRUCTURE ACTIVITY RELATION;

ANIMALS; BENZOIN; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; DRUG DESIGN; PROPANE; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 77955549965     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.05.058     Document Type: Article

References (23)

1. S. Fiorucci, R. Meli, M. Bucci, and G. Cirino Biochem. Pharmacol. 62 2001 1433 1438
2. J.R. Vane Nature 231 1971 232 237 239
3. J.Y. Fu, J.L. Masferrer, K. Seibert, A. Raz, and P. Needleman J. Biol. Chem. 265 1990 16736 16737
4. C.S. Williams, and R.N. DuBois Am. J. Physiol. 270 1996 393 400
5. P.C. Konturek, J. Kania, G. Burnat, E.G. Hahn, and S.J. Konturek J. Physiol. Pharmacol. 56 2005 57 73
6. M.M. Goldenberg Clin. Ther. 21 1999 1497 1513
7. T. Kawamori, C.V. Rao, K. Seibert, and B.S. Reddy Cancer Res. 58 1998 409
8. M. Katori, and M. Majima Inflamm. Res. 295 2000 802 809
9. J.R. Vane, and R.M. Botting Inflamm. Res. 47 1998 S78 S87
10. J.J. Talley Prog. Med. Chem. 36 1999 201 234
11. J.M. Dogné, C.T. Supuran, and D. Pratico J. Med. Chem. 48 2005 2251 2257
12. M.J. Uddin, P.N. Praveen Rao, and E.E. Knaus Bioorg. Med. Chem. Lett. 14 2004 1953 1956
13. M.J. Uddin, P.N. Praveen Rao, E.E. Knaus, and R. McDonald J. Med. Chem. 47 2004 6108 6111
14. M.J. Uddin, P.N. Praveen Rao, M.A. Rahim, R. McDonald, and E.E. Knaus Bioorg. Med. Chem. Lett. 14 2004 4911 4914
15. P.N. Praveen Rao, Q.H. Chen, and E.E. Knaus Bioorg. Med. Chem. Lett. 15 2005 4842 4845
16. A. Zarghi, S. Kakhgi, A. Hadipoor, B. Daraee, O.G. Dadrass, and M. Hedayati Bioorg. Med. Chem. Lett. 18 2008 1336 1339
17. A. Zarghi, S. Arfaee, P.N. Praveen Rao, and E.E. Knaus Bioorg. Med. Chem. 14 2006 2600 2605
18. A. Zarghi, T. Zebardast, F. Hakimion, F.H. Shirazi, P.N. Praveen Rao, and E.E. Knaus Bioorg. Med. Chem. 14 2006 7044 7050
19. S. Mittal, S. Durani, and R.S. Kapil J. Med. Chem. 28 1985 492 497
20. P.J. Duke, and D.W. Boykin J. Org. Chem. 37 1972 1436 1439
21. M. Therien, J.Y. Gauthier, Y. Leblanc, S. Leger, H. Perrier, P. Prasit, and Z. Wang Synthesis 12 2001 1778 1779
22. S.K. Singh, V. Saibaba, V. Ravikumar, C.S. Rao, V. Akhila, and Y.K. Rao Bioorg. Med. Chem. 12 2004 1881 1893
23. A. Zarghi, L. Najafnia, B. Daraee, O.G. Dadrass, and M. Hedayati Bioorg. Med. Chem. Lett. 17 2007 5634 5637