Synthesis, biological evaluation and molecular modeling of dihydro-pyrazolyl-thiazolinone derivatives as potential COX-2 inhibitors

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 22, 2012, Pages 6648-6654

  Qiu, Ke Ming ^a   Yan, Ru ^a   Xing, Man ^a   Wang, Hai Hong ^a   Cui, Hong En ^a   Gong, Hai Bin ^b   Zhu, Hai Liang ^a  

^a NANJING UNIVERSITY   (China)

^b XUZHOU CENTRAL HOSPITAL   (China)

Author keywords

Anti inflammatory; COX 2; Pyrazole; Thiazolinone

Indexed keywords

2 [3 (3,4 DICHLOROPHENYL) 5 (2 TOYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL]THIAZOL 4(5H) ONE; 2 [3 (3,4 DICHLOROPHENYL) 5 (4 FLUOROPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL]THIAZOL 4(5H) ONE; 2 [3 (3,4 DICHLOROPHENYL) 5 (4 METHOXYPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL]THIAZOL 4(5H) ONE; 2 [3 (3,4 DICHLOROPHENYL) 5 (4 TOLYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL]THIAZOL 4(5H) ONE; 2 [3 (3,4 DICHLOROPHENYL) 5 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL]THIAZOL 4(5H) ONE; 2 [3 (3,4 DIMETHYLPHENYL) 5 (2 TOLYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL]THIAZOL 4(5H) ONE; 2 [3 (3,4 DIMETHYLPHENYL) 5 (3 TOLYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL]THIAZOL 4(5H) ONE; 2 [3 (3,4 DIMETHYLPHENYL) 5 (4 FLUOROPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL]THIAZOL 4(5H) ONE; 2 [3 (3,4 DIMETHYLPHENYL) 5 (4 METHOXYPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL]THIAZOL 4(5H) ONE; 2 [3 (3,4 DIMETHYLPHENYL) 5 (4 TOLYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL]THIAZOL 4(5H) ONE; 2 [3 (3,4 DIMETHYLPHENYL) 5 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL]THIAZOL 4(5H) ONE; 2 [5 (2 CHLOROPHENYL) 3 (3,4 DICHLOROPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL]THIAZOL 4(5H) ONE; 2 [5 (2 CHLOROPHENYL) 3 (3,4 DIMETHYLPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL]THIAZOL 4(5H) ONE; 2 [5 (3 CHLOROPHENYL) 3 (3,4 DICHLOROPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL]THIAZOL 4(5H) ONE; 2 [5 (3 CHLOROPHENYL) 3 (3,4 DIMETHYLPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL]THIAZOL 4(5H) ONE; 2 [5 (4 BROMOPHENYL) 3 (3,4 DIMETHYLPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL]THIAZOL 4(5H) ONE; 2 [5 (4 CHLOROPHENYL) 3 (3,4 BROMOPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL]THIAZOL 4(5H) ONE; 2 [5 (4 CHLOROPHENYL) 3 (3,4 DICHLOROPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL]THIAZOL 4(5H) ONE; 2 [5 (4 CHLOROPHENYL) 3 (3,4 DIMETHYLPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL]THIAZOL 4(5H) ONE; CELECOXIB; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; DIHYDROPYRAZOLYLTHIAZOLINONE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; CYTOTOXICITY; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; MOLECULAR DOCKING; MOLECULAR MODEL; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALS; BINDING SITES; CATALYTIC DOMAIN; CELL LINE; CELL SURVIVAL; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; MICE; MOLECULAR DOCKING SIMULATION; PYRAZOLES; THIAZOLES;

EID: 84867843793     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.09.021     Document Type: Article

References (28)

1. J. Wallace Trends Pharmacol. Sci. 28 2007 501
2. G. Dannhardt, W. Kiefer, G. Krämer, S. Maehrlein, U. Nowe, and B. Fiebich Eur. J. Med. Chem. 35 2000 499
3. S. Fiorucci, L. Santucci, and E. Distrutti Dig. Liver Dis. 39 2007 1043
4. M.R. Griffin, A. Yared, and W.A. Ray Am. J. Epidemiol. 151 2000 488
5. J.R. Vane, and R.M. Botting Inflamm. Res. 47 1998 S78
6. M. Diana, C.B. Isaza-Guzmán, M.P. Teller-Carrero, L.V. Laberry-Bermúdez, S.I. González-Pérez, and Tobón-Arroyave Arch. Oral Biol. 57 2012 503
7. F. Julémont, X.D. Leval, C. Michaux, J.F. Renardc, J.Y. Winum, J.L. Montero, J. Damas, J.M. Dogné, and B. Pirotte J. Med. Chem. 47 2004 6749
8. T.D. Warner, F. Giuliano, I. Vojnovic, A. Bukasa, J.A. Mitchell, and J.R. Vane Proc. Natl. Acad. Sci. U.S.A. 96 1999 7563
9. J.R. Vane, Y.S. Bakhle, and R.M. Botting Annu. Rev. Pharmacol. Toxicol. 38 1998 97
10. B.S. Mary, G. Kamara, P. Esmeralda, C.L. Maggie, and M. Kylie Pharmacol. Res. 65 2012 445
11. N.V. Cunha, S.B. de Abreu, C. Panis, S. Grassiolli, F.A. Guarnier, R. Cecchini, T.L. Mazzuco, P. Pinge-Filho, and M.C. Martins-Pinge Life Sci. 87 2010 375
12. C.F. Bocca, A. Bozzo, and A.M. Bassignana Anticancer Res. 30 2010 2659
13. H.A. Park, K. Lee, S.J. Park, B. Ahn, J.C. Lee, H.Y. Cho, and K.I. Lee Bioorg. Med. Chem. Lett. 15 2005 3307
14. A. Tanitame, Y. Oyamada, K. Ofuji, M. Fujimoto, N. Iwai, Y. Hiyama, K. Suzuki, H. Ito, M. Wachi, and J. Yamagishi J. Med. Chem. 47 2004 3693
15. G. Szabo, J. Fischer, A. Kis-Varga, and K. Gyires J. Med. Chem. 51 2008 142
16. S.M. Rida, M.N.S. Saudi, A.M. Youssef, and M.A. Halim Lett. Org. Chem. 6 2009 282
17. M.G. Brasca, C.R. Albanese, R. Amici, D. Ballinari, L. Corti, V. Croci, D. Fancelli, F. Fiorentini, M. Nesi, P. Orsini, F. Orzi, W. Pastori, E. Perrone, E. Pesenti, P. Pevarello, F. Riccardi-Sirtori, F. Roletto, P. Roussel, M. Varasi, A. Vulpetti, and C. Mercurio ChemMedChem 2 2007 841
18. A.K. Tewari, and A. Mishra Bioorg. Med. Chem. 3 2001 715
19. A. Palomer, F. Cabre, J. Pascual, J. Campos, M.A. Trujillo, A. Entrena, M.A. Gallo, L. Garcia, D. Mauleon, and A. Espinosa J. Med. Chem. 45 2002 1402
20. R. Ottana, R. Maccari, M.L. Barreca, G. Bruno, A. Rotondo, A. Rossi, G. Chiricosta, R. Di Paola, L. Sautebin, S. Cuzzocrea, and M.G. Vigorita Bioorg. Med. Chem. 13 2005 4243
21. V. Gududuru, E. Hurh, J.T. Dalton, and D.D. Miller Bioorg. Med. Chem. Lett. 14 2004 5289
22. E. Rydzik, A. Szadowska, and A. Kaminska Acta Pol. Pharm. 41 1984 459
23. A.A. Geronikaki, A.A. Lagunin, D.I. Hadjipavlou-Litina, P.T. Eleftheriou, D.A. Filimonov, V.V. Poroikov, I. Alam, and A.K. Saxena J. Med. Chem. 51 2008 1601
24. R. Maccari, M.L. Barreca, G. Bruno, A. Rotondo, A. Rossi, G. Chiricosta, R.D. Paola, L. Sautebin, S. Cuzzocread, M.G. Vigorita, and R. Ottana Biol. Med. Chem 13 2005 4243
25. Q.W. Xie, R. Whisnant, and C. Nathan J. Exp. Med. 177 1993 1779
26. 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
27. J.K. Gierse, J.J. McDonald, S.D. Hauser, S.H. Rangwala, C.M. Kobolt, and K. Seibert J. Biol. Chem. 271 1996 15810
28. A.G. Amr, and M.M. Abdulla Bioorg. Med. Chem. 14 2006 4341