Celecoxib analogs bearing benzofuran moiety as cyclooxygenase-2 inhibitors: Design, synthesis and evaluation as potential anti-inflammatory agents

European Journal of Medicinal Chemistry

Volumn 76, Issue , 2014, Pages 482-493

  Hassan, Ghaneya Sayed ^a   Abou Seri, Sahar Mahmoud ^a   Kamel, Gehan ^b   Ali, Mamdouh Moawad ^c  

^a CAIRO UNIVERSITY   (Egypt)

^b Cairo University   (Egypt)

^c NATIONAL RESEARCH CENTRE   (Egypt)

Author keywords

Anti inflammatory agents; Benzofuran; Celecoxib analogs; COX 1 COX 2 inhibitory activity; Pyrazole

Indexed keywords

(4,6 DIMETHOXYBENZOFURAN 5 YL)(3 PHENYLOXIRAN 2 YL)METHANONE; (E) 3 (4 CHLOROPHENYL) 1 (4,6 DIMETHOXYBENZOFURAN 5 YL)PROP 2 EN 1 ONE; (E) 3 (4 FLUOROPHENYL) 1 (4,6 DIMETHOXYBENZOFURAN 5 YL)PROP 2 EN 1 ONE; 4 [3 (4,6 DIMETHOXYBENZOFURAN 5 YL) 5 PHENYL 1H PYRAZOL 1 YL]BENZENE SULFONAMIDE; 4 [5 (4 CHLOROPHENYL) 3 (4,6 DIMETHOXYBENZOFURAN 5 YL) 1H PYRAZOL 1 YL]BENZENE SULFONAMIDE; 4 [5 (4 TRIFLUOROMETHYLPHENYL) 3 (4,6 DIMETHOXYBENZOFURAN 5 YL) 1H PYRAZOL 1 YL]BENZENE SULFONAMIDE; 4 [5 (6 HYDROXY 4 METHOXYBENZOFURAN 5 YL) 3 (PYRIDIN 3YL) 1H PYRAZOL 1 YL]BENZENE SULFONAMIDE; 4 [5 (6 HYDROXY 4 METHOXYBENZOFURAN 5 YL) 3 METHYL 1H PYRAZOL 1 YL]BENZENE SULFONAMIDE; 4 [5 (6 HYDROXY 4 METHOXYBENZOFURAN 5 YL) 3 TRIFLUOROMETHYL 1H PYRAZOL 1 YL BENZENE SULFONAMIDE; 4 [5 (6 HYDROXY 4,7 DIMETHOXYBENZOFURAN 5 YL) 3 (PYRIDIN 3 YL) 1H PYRAZOL 1 YL]BENZENE SULFONAMIDE; 4 [5 (6 HYDROXY 4,7 DIMETHOXYBENZOFURAN 5 YL) 3 TRIFLUOROMETHYL 1H PYRAZOL 1 YL]BENZENE SULFONAMIDE; 4,4,4 TRIFLUORO 1 (6 HYDROXY 4 METHOXYBENZOFURAN 5 YL)BUTANE 1,3 DIONE; 4,4,4 TRIFLUORO 1 (6 HYDROXY 4,7 DIMETHOXYBENZOFURAN 5 YL)BUTANE 1,3 DIONE; [3 (4 CHLOROPHENYL)OXIRAN 2 YL](4,6 DIMETHOXYBENZOFURAN 5 YL)METHANONE; [3 (4 FLUOROPHENYL)OXIRAN 2 YL](4,6 DIMETHOXYBENZOFURAN 5 YL)METHANONE; ANTIINFLAMMATORY AGENT; BENZOFURAN DERIVATIVE; CELECOXIB; IBUPROFEN; UNCLASSIFIED DRUG; {3 [4 (TRIFLUOROMETHYL)PHENYL]OXIRAN 2 YL}(4,6 DIMETHOXYBENZOFURAN 5 YL)METHANONE; CYCLOOXYGENASE 2 INHIBITOR; PYRAZOLE DERIVATIVE; SULFONAMIDE;

ANIMAL EXPERIMENT; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG DESIGN; DRUG SAFETY; DRUG SCREENING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; IN VIVO STUDY; MOLECULAR DOCKING; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; ULCEROGENESIS; ANIMAL; CHEMISTRY; MALE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; WISTAR RAT;

ANIMALS; ANTI-INFLAMMATORY AGENTS; BENZOFURANS; CYCLOOXYGENASE 2 INHIBITORS; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MOLECULAR DOCKING SIMULATION; PYRAZOLES; RATS; RATS, WISTAR; SULFONAMIDES;

EID: 84901734869     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.02.033     Document Type: Article

References (53)

1. D.A. Williams, and T.L. Lemke Non-steroidal anti-inflammatory drugs D.A. Williams, Foye's Principles of Medicinal Chemistry fifth ed. 2002 Lippincott Williams & Wilkins 751 793
2. P. Gund, and T.Y. Shen Journal of Medicinal Chemistry 20 1977 1146 1152
3. J.Y. Jouzeau, B. Terlain, A. Abid, E. Nedelec, and P. Netter Drugs 53 1997 563 582
4. H. Yoshimura, S. Sekine, H. Adachi, Y. Uematsu, A. Mitani, N. Futaki, and N. Shimizu Protein Expression and Purification 80 2011 41 46
5. B. Yao, J. Xu, R.C. Harris, and M.Z. Zhang American Journal of Physiology - Renal Physiology 294 2008 433 439
6. H. Haruna, T. Shimizu, Y. Ohtsuka, Y. Yarita, T. Fujii, T. Kudo, and Y. Yamashiro Pediatrics International 50 2008 1 6
7. S. Yoshida, M. Ujiki, X.Z. Ding, C. Pelman, M.S. Talamonti, R.H. Bell, W. Denham, and T.E. Adrian Molecular Cancer 4 2005 27
8. M.G. Perrone, A. Scilimati, L. Simone, and P. Vitale Current Medicinal Chemistry 17 2010 3769 3805
9. P. Vitale, S. Tacconelli, M.G. Perrone, P. Malerba, L. Simone, A. Scilimati, A. Lavecchia, M. Dovizio, E. Marcantoni, A. Bruno, and P. Patrignani Journal of Medicinal Chemistry 56 2013 4277 4299
10. K.G. Peri, P. Hardy, D.Y. Li, D.R. Varma, and S. Chemtob Journal of Biological Chemistry 270 1995 24615 24620
11. A.L. Sampaio, J. Dalli, V. Brancaleone, F. D'Acquisto, M. Perretti, and C. Wheatley Mediators of Inflammation 2013 2013 741804
12. R. Calvello, M.A. Panaro, M.L. Carbone, A. Cianciulli, M.G. Perrone, P. Vitale, P. Malerba, and A. Scilimati Pharmacological Research 65 2012 137 148
13. L.A. Garcia-Rodriguez, and S. Hernández-Diaz Epidemiology 14 2003 240 246
14. C.H. Ruan, S.P. So, and K.H. Ruan Life Sciences 88 2011 24 30
15. M. Khan, and A. Fraser Irish Medical Journal 105 2012 119 121
16. W.B. Whyte, G. Faich, J.S. Borer, and R.W. Makuch American Journal of Cardiology 92 2003 411 418
17. N.M. Davies, A.J. McLachlan, R.O. Day, and K.M. Williams Clinical Pharmacokinetics 38 2000 225 242
18. J. Castellsague, N. Riera-Guardia, B. Calingaert, C. Varas-Lorenzo, A. Fourrier-Reglat, F. Nicotra, M. Sturkenboom, and S. Perez-Gutthann Drug Safety 35 2012 1127 1146
19. A.S. Kalgutkar, B.C. Crews, S.W. Rowlinson, A.B. Marnett, K.R. Kozak, R.P. Remmel, and L.J. Marnett Proceedings of the National Academy of Sciences of the United States of America 97 2000 925 930
20. L. Di Nunno, P. Vitale, A. Scilimati, S. Tacconelli, and P. Patrignani Journal of Medicinal Chemistry 47 2004 4881 4890
21. T.D. Penning, J.J. Talley, S.R. Bertenshaw, J.S. Carter, P.W. Collins, S. Docter, 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 Journal of Medicinal Chemistry 40 1997 1347 1365
22. O.L. Lorens, J.J. Perez, A. Palomer, and D. Mauleon Journal of Molecular Graphics and Modelling 20 2002 359 371
23. M. Zheng, Z. Zhang, W. Zhu, H. Liu, X. Luo, K. Chen, and H. Jiang Bioorganic and Medicinal Chemistry 14 2006 3428 3437
24. J.M. Janusz, P.A. Young, J.M. Ridgeway, M.W. Scherz, K. Enzweiler, L.I. Wu, L. Gan, J. Chen, D.E. Kellstein, S.A. Green, J.L. Tulich, T. Rosario-Jansen, I.J. Magrisso, K.R. Wehmeyer, D.L. Kuhlenbeck, T.H. Eichhold, and R.L. Dobson Journal of Medicinal Chemistry 41 1998 3515 3529
25. R. Deshpande, M. Bhagawan Raju, S. Parameshwar, S.M. Shanth Kumar, S. Appalaraju, S. Manjunath, and S.M. Yelagatti American Journal of Chemistry 2 2012 115 120
26. G.S. Hassan, and G.A. Soliman European Journal of Medicinal Chemistry 45 2010 4104 4112
27. F.A. Ragab, G.S. Hassan, H.A. Yossef, and H.A. Hashem European Journal of Medicinal Chemistry 42 2007 1117 1127
28. G.O. Dengiz, F. Odabasoglu, Z. Halici, H. Suleyman, E. Cadirci, and Y. Bayir Archives of Pharmacal Research 30 2007 1426 1434
29. T.A. Geissman, and D.K. Fukushima Journal of the American Chemical Society 70 1948 1686 1689
30. E. Weitz, and A. Scheffer Berichte 54 1921 2327 2344
31. Y. Apeloig, M. Karni, and Z. Rapoport Journal of the American Chemical Society 105 1983 2784 2793
32. R. Turner Screening Method in Pharmacology. Anti-inflammatory Agent 13 1965 Academic Press New York London 158
33. M. Meshali, E. El-Sabbah, and A. Foda Acta Pharmaceutica Technologica 29 1983 217 230
34. A. Robert, J.E. Nezamis, and J.P. Phillips Gastroenterology 55 1968 481 487
35. E.J. Freireich, E.A. Gehan, D.P. Rall, L.H. Schmidt, and H.E. Skipper Cancer Chemotherapy Reports 50 1966 219 244
36. J.L. Wang, D. Limburg, M.J. Graneto, J. Springer, J.R. Hamper, S. Liao, J.L. Pawlitz, R.G. Kurumbail, T. Maziasz, J.J. Talley, J.R. Kiefer, and J. Carter Bioorganic & Medicinal Chemistry Letters 20 2010 7159 7163
37. MOE, Chemical Computing Group, Inc., Montreal, http://www.chemcomp.com.
38. R.G. Kurumbail, A.M. Stevens, J.K. Gierse, J.J. McDonald, R.A. Stegeman, J.Y. Pak, D. Gildehaus, J.M. Miyashiro, T.D. Penning, K. Seibert, P.C. Isakson, and W.C. Stallings Nature 384 1996 644 648
39. S.W. Rowlinson, J.R. Kiefer, J.J. Prusakiewicz, J.L. Pawlitz, K.R. Kozak, A.S. Kalgutkar, W.C. Stallings, R.G. Kurumbail, and L.J. Marnett Journal of Biological Chemistry 46 2003 45763 456769
40. A. DerHovanessian, J.B. Doyon, A. Jain, P.R. Rablen, and A.M. Sapse Org. Lett. 1 1999 1359 1362
41. Laurent Schaeffer C.,G. Wermuth, The Role of Functional Groups in Drug Receptor Interaction; The Practice of Medicinal Chemistry third ed. 2008 Elsevier Ltd 464 479
42. P.N. Rao, Q.H. Chen, and E.E. Knaus Journal of Medicinal Chemistry 49 2006 1668 1683
43. Y. Harrak, G. Casula, J. Basset, G. Rosell, S. Plescia, D. Raffa, M.G. Cusimano, R. Pouplana, and M.D. Pujol Journal of Medicinal Chemistry 53 2010 6560 6571
44. Molinspiration Cheminformatics (http://www.molinspiration.com/cgi-bin/ properties).
45. C.A. Lipinski, F. Lombardo, B.W. Dominy, and P.J. Feeney Advanced Drug Delivery Reviews 46 2001 3 26
46. P.R. Duchowicz, A. Talevi, C. Bellera, L.E. Bruno-Blanch, and E.A. Castro Bioorganic and Medicinal Chemistry 15 2007 3711 3719
47. D.B. Jack, J.L. Hawker, L. Rooney, M. Beerahee, J. Lobo, and P. Patel Journal of Chromatography 452 1988 257 264
48. E. Spath, and W. Gruber Ber 71 1938 106 113
49. A. Schönberg, and A. Sina Journal of the American Chemical Society 72 1950 1611 1616
50. A. Schönberg, N. Badran, and N.A. Starkowsky Journal of the American Chemical Society 77 1955 5430 5431
51. A. Schönberg, N. Badran, and N.A. Starkowsky Journal of the American Chemical Society 75 1953 4992 4995
52. O.M. Abdel Hafez, K.H.M. Ahmed, and E.E. Haggag Molecules 6 2001 396 405
53. M. Zimmermann Pain 6 1983 109 110