Design, synthesis, and biological evaluation of linear 1-(4-, 3- or 2-methylsulfonylphenyl)-2-phenylacetylenes: A novel class of cyclooxygenase-2 inhibitors

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 23, 2005, Pages 6425-6434

  Chen, Qiao Hong ^a   Rao, P N Praveen ^a   Knaus, Edward E ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

1 (Methylsulfonylphenyl) 2 phenylacetylenes; Anti inflammatory and analgesic activities; Cyclooxygenase 2 inhibitors; Sonogashira coupling reaction

Indexed keywords

1 (2 METHYLSULFONYLPHENYL) 2 (3 ACETOXYPHENYL)ACETYLENE; 1 (2 METHYLSULFONYLPHENYL) 2 (3 FLUOROPHENYL)ACETYLENE; 1 (2 METHYLSULFONYLPHENYL) 2 (3 HYDROXYPHENYL)ACETYLENE; 1 (2 METHYLSULFONYLPHENYL) 2 (3 METHOXYPHENYL)ACETYLENE; 1 (2 METHYLSULFONYLPHENYL) 2 PHENYLACETYLENE; 1 (3 METHYLSULFONYLPHENYL) 2 (3 ACETOXYPHENYL)ACETYLENE; 1 (3 METHYLSULFONYLPHENYL) 2 (3 FLUOROPHENYL)ACETYLENE; 1 (3 METHYLSULFONYLPHENYL) 2 (3 HYDROXYPHENYL)ACETYLENE; 1 (3 METHYLSULFONYLPHENYL) 2 (3 METHOXYPHENYL)ACETYLENE; 1 (3 METHYLSULFONYLPHENYL) 2 (4 METHYLPHENYL)ACETYLENE; 1 (3 METHYLSULFONYLPHENYL) 2 PHENYLACETYLENE; 1 (4 METHYLSULFONYLPHENYL) 2 (3 ACETOXYPHENYL)ACETYLENE; 1 (4 METHYLSULFONYLPHENYL) 2 (3 FLUOROPHENYL)ACETYLENE; 1 (4 METHYLSULFONYLPHENYL) 2 (3 HYDROXYPHENYL)ACETYLENE; 1 (4 METHYLSULFONYLPHENYL) 2 (3 METHOXYPHENYL)ACETYLENE; 1 (4 METHYLSULFONYLPHENYL) 2 (4 METHYLPHENYL)ACETYLENE; 1 (4 METHYLSULFONYLPHENYL) 2 PHENYLACETYLENE; ACETYLENE DERIVATIVE; CARRAGEENAN; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; PALLADIUM; ROFECOXIB; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; BINDING SITE; CATALYSIS; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; ENZYME BINDING; ENZYME INHIBITION; IC 50; ISOENZYME ANALYSIS; NONHUMAN; OXIDATION; PAW EDEMA; RAT; SONOGASHIRA REACTION; STRUCTURE ACTIVITY RELATION;

ACETYLENE; ANALGESICS; ANIMALS; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; DRUG DESIGN; METHYLATION; MOLECULAR STRUCTURE; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFATES;

ANIMALIA;

EID: 27544464264     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.06.064     Document Type: Article

References (23)

1. T.D. Penning, J.J. Tally, S.R. Bertenshaw, J.S. Carter, P.W. Collins, S. Doctor, M.J. Graneto, L.F. Lee, J.W. Malecha, J.M. Miyashiro, R.S. Rogers, D.J. Rogier, S.S. Yu, G.D. Anderson, E.G. Burton, J.N. Cogburn, S.A. Gregory, C.M. Koboldt, W.E. Perkins, K. Seibert, A.W. Veenhuizen, Y.Y. Zhang, and P.C. Isakson J. Med. Chem. 40 1997 1347
2. P. Prasit, Z. Wang, C. Brideau, C.C. Chan, S. Charleson, W. Cromlish, D. Ethier, J.F. Evans, A.W. Ford-Hutchinson, J.Y. Gauthier, R. Gordon, J. Guay, M. Gresser, S. Kargman, B. Kennedy, Y. Leblanc, S. Leger, J. Mancini, G.P. O'Neill, M. Quellet, M.D. Percival, H. Perrier, D. Riendeau, I. Rodger, P. Tagari, M. Therien, P. Vickers, E. Wong, L.J. Xu, R.N. Young, R. Zamboni, S. Boyce, N. Rupniak, M. Forrest, D. Visco, and D. Patrick Bioorg. Med. Chem. Lett. 9 1999 1773
3. J.A. Talley, D.L. Brown, J.S. Carter, M.J. Masferrer, W.E. Perkins, R.S. Rogers, A.F. Shaffer, Y.Y. Zhang, B.S. Zweifel, and K. Seiberk J. Med. Chem. 43 2000 775
4. D. Riendeau, M.D. Percival, C. Brideau, S. Charleson, D. Dube, D. Ethier, J.-P. Falgueyret, R.W. Friesen, R. Gordon, G. Greig, I. Guay, J. Manacini, M. Ouellet, E. Wong, L. Xu, S. Boyce, D. Visco, Y. Girad, P. Prasit, R. Zamboni, J.W. Rodger, M. Gresser, A.W. Ford-Hutchinson, R.N. Young, and C.-C. Chan J. Pharmacol. Exp. Ther. 296 2001 558
5. I.W. Davies, J.-F. Marcoux, E.G. Corley, M. Journet, D.-W. Cai, M. Palucki, J. Wu, R.D. Larsen, K. Rossen, P.J. Pye, L. Dimichele, P. Dormer, and P.J. Reider J. Org. Chem. 65 2000 8415
6. M.E. Turini, and R.N. DuBois Ann. Rev. Med. 53 2002 35
7. C.R. Rodrigues, M.P. Veloso, H. Verli, C.A. Fraga, A.L. Miranda, and E. Barreiro J. Curr. Med. Chem. 9 2002 849
8. C. Bombardier, L. Laine, A. Reicin, D. Shapiro, R. Burgos-Vargas, B. Davies, R. Day, M.B. Ferraz, C.J. Hawkey, M.C. Hochberg, T.K. Kvien, and T.J. Schnitzer N. Engl. J. Med. 343 2000 1520
9. F.E. Silverstein, G. Faich, J.L. Goldstein, L.S. Simon, T. Pincus, A. Whelton, R. Makuch, G. Eisen, N.M. Agrawa, F.W. Stenson, A.M. Burr, W.W. Zhao, J.D. Kent, J.B. Lefkwith, K.M. Verburg, and G.S. Geis JAMA 284 2000 1247
10. J. Talley Prog. Med. Chem. 36 1999 201
11. J.M. Dogné, C.T. Supuran, and D. Pratico J. Med. Chem. 48 2005 2251
12. M.J. Uddin, P.N.P. Rao, and E.E. Knaus Bioorg. Med. Chem. Lett. 14 2004 1953
13. M.J. Uddin, P.N.P. Rao, and E.E. Knaus Bioorg. Med. Chem. 12 2004 5929
14. M.J. Uddin, P.N.P. Rao, M.A. Rahim, R. McDonald, and E.E. Knaus Bioorg. Med. Chem. Lett. 14 2004 4911
15. M.J. Uddin, P.N.P. Rao, and E.E. Knaus Bioorg. Med. Chem. 13 2005 417
16. M.J. Uddin, P.N.P. Rao, R. McDonald, and E.E. Knaus Bioorg. Med. Chem. Lett. 15 2005 439
17. M.J. Uddin, P.N.P. Rao, E.E. Knaus, and R. McDonald J. Med. Chem. 47 2004 6108
18. S. Takahashi, Y. Kuroyama, K. Sonogashira, and N. Hagihara Synthesis 1980 627
19. R.C. Larock, and L.W. Harrison J. Am. Chem. Soc. 106 1984 4218
20. O. Mongin, C. Papamicael, N. Hoyler, and A. Gossauer J. Org. Chem. 63 1998 5568
21. R.P. Hsung, J.R. Babcock, C.E.D. Chiddsey, and L.R. Sita Tetrahedron Lett. 36 1995 4525
22. C.A. Winter, E.A. Risley, and G.W. Nuss Proc. Soc. Exp. Biol. Med. 111 1962 544
23. K. Fukawa, O. Kawano, M. Hibi, N. Misaka, S. Ohba, and Y. Hatanaka J. Pharmacol. Methods 4 1980 251