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Volumn 14, Issue 4, 2006, Pages 918-927

Synthesis, molecular modelling and enzymatic evaluation of (±)3,5-diphenyl-2-thioxoimidazolidin-4-ones as new potential cyclooxygenase inhibitors

Author keywords

2 Thioxoimidazolin 4 ones; COX inhibition; Human COX 2; Ovine COX 1

Indexed keywords

3 (3 BROMOPHENYL) 5 PHENYL 2 THIOXOIMIDAZOLIDIN 4 ONE; 3 (3 CHLOROPHENYL) 5 PHENYL 2 THIOXOIMIDAZOLIDIN 4 ONE; 3 (3 FLUOROPHENYL 5 PHENYL) 2 THIOXOIMIDAZOLIDIN 4 ONE; 3 (3 IODOPHENYL) 5 PHENYL 2 THIOXOIMIDAZOLIDIN 4 ONE; 3 (3 METHOXYPHENYL) 5 PHENYL 2 THIOXOIMIDAZOLIDIN 4 ONE; 3 (3 METHYLPHENYL) 5 PHENYL 2 THIOXOIMIDAZOLIDIN 4 ONE; 3 (4 BROMOPHENYL) 5 PHENYL 2 THIOXOIMIDAZOLIDIN 4 ONE; 3 (4 CHLOROPHENYL) 5 PHENYL 2 THIOXOIMIDAZOLIDIN 4 ONE; 3 (4 ETHYLPHENYL) 5 PHENYL 2 THIOXOIMIDAZOLIDIN 4 ONE; 3 (4 FLUOROPHENYL) 5 PHENYL 2 THIOXOIMIDAZOLIDIN 4 ONE; 3 (4 IODOPHENYL) 5 PHENYL 2 THIOXOIMIDAZOLIDIN 4 ONE; 3 (4 METHYLPHENYL) 5 PHENYL 2 THIOXOIMIDAZOLIDIN 4 ONE; 3 (4 NITROPHENYL) 5 PHENYL 2 THIOXOIMIDAZOLIDIN 4 ONE; 3 [3 (METHYLSULFONYL)PHENYL] 5 PHENYL 2 THIOXOIMIDAZOLIDIN 4 ONE; 3 [4 (AMINOSULFONYL)PHENYL] 5 PHENYL 2 THIOXOIMIDAZOLIDIN 4 ONE; 3 [4 (METHYLSULFONYL)PHENYL] 5 PHENYL 2 THIOXOIMIDAZOLIDIN 4 ONE; 3,5 DIPHENYL 2 THIOXOIMIDAZOLIDIN 4 ONE; 3,5 DIPHENYL 2 THIOXOIMIDAZOLIDIN 4 ONE DERIVATIVE; 5 PHENYL 2 THIOXO 3 [3 (TRIFLUOROMETHYL)PHENYL]IMIDAZOLIDIN 4 ONE; 5 PHENYL 2 THIOXO 3 [4 (TRIFLUOROMETHYL)PHENYL]IMIDAZOLIDIN 4 ONE; CELECOXIB; CYCLOOXYGENASE 2; ETORICOXIB; IMIDAZOLINE DERIVATIVE; LIPOPOLYSACCHARIDE; NIMESULIDE; PROSTAGLANDIN SYNTHASE INHIBITOR; RECOMBINANT ENZYME; ROFECOXIB; UNCLASSIFIED DRUG; VALDECOXIB;

EID: 30344431808     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.09.005     Document Type: Article
Times cited : (24)

References (44)
  • 1
    • 0024558198 scopus 로고
    • The eicosanoids and their biochemical mechanisms of action
    • W.L. Smith The eicosanoids and their biochemical mechanisms of action Biochem. J. 259 1989 315
    • (1989) Biochem. J. , vol.259 , pp. 315
    • Smith, W.L.1
  • 3
    • 0025365504 scopus 로고
    • Cyclooxygenase is an immediate-early gene induced by interleukin-1 in human endothelial cells
    • J.A. Maier, T. Hla, and T. Maciag Cyclooxygenase is an immediate-early gene induced by interleukin-1 in human endothelial cells J. Biol. Chem. 265 1990 10805
    • (1990) J. Biol. Chem. , vol.265 , pp. 10805
    • Maier, J.A.1    Hla, T.2    MacIag, T.3
  • 4
    • 0026744831 scopus 로고
    • Purification and characterization of a novel, distinct isoform of prostaglandin endoperoxide synthase induced by human chorionic gonadotropin in granulosa cells of rat preovulatory follicles
    • J. Sirois, and J.S. Richards Purification and characterization of a novel, distinct isoform of prostaglandin endoperoxide synthase induced by human chorionic gonadotropin in granulosa cells of rat preovulatory follicles J. Biol. Chem. 267 1992 6382
    • (1992) J. Biol. Chem. , vol.267 , pp. 6382
    • Sirois, J.1    Richards, J.S.2
  • 6
    • 0029950418 scopus 로고    scopus 로고
    • Transcriptional regulation of prostaglandin synthase 2 gene expression by platelet-derived growth factor and serum
    • W. Xie, and H.R. Herschman Transcriptional regulation of prostaglandin synthase 2 gene expression by platelet-derived growth factor and serum J. Biol. Chem. 271 1996 31742
    • (1996) J. Biol. Chem. , vol.271 , pp. 31742
    • Xie, W.1    Herschman, H.R.2
  • 14
    • 0035246513 scopus 로고    scopus 로고
    • Cyclooxygenase inhibitors-current status and future prospects
    • G. Dannhardt, and W. Kiefer Cyclooxygenase inhibitors-current status and future prospects Eur. J. Med. Chem. 36 2001 109
    • (2001) Eur. J. Med. Chem. , vol.36 , pp. 109
    • Dannhardt, G.1    Kiefer, W.2
  • 15
    • 8644251351 scopus 로고    scopus 로고
    • A new class of acyclic 2-alkyl-1,1,2-triaryl (Z)-olefins as selective cyclooxygenase-2 inhibitors
    • M.J. Uddin, P.N. Praveen Rao, R. McDonald, and E.E. Knaus A new class of acyclic 2-alkyl-1,1,2-triaryl (Z)-olefins as selective cyclooxygenase-2 inhibitors J. Med. Chem. 7 2004 6108
    • (2004) J. Med. Chem. , vol.7 , pp. 6108
    • Uddin, M.J.1    Praveen Rao, P.N.2    McDonald, R.3    Knaus, E.E.4
  • 19
    • 0037187427 scopus 로고    scopus 로고
    • 4-(4-Cycloalkyl/aryl-oxazol-5-yl)benzenesulfonamides as selective cyclooxygenase-2 inhibitors: Enhancement of the selectivity by introduction of a fluorine atom and identification of a potent, highly selective, and orally active COX-2 inhibitor JTE-522
    • H. Hashimoto, K. Imamura, J. Haruta, and K. Wakitani 4-(4-Cycloalkyl/ aryl-oxazol-5-yl)benzenesulfonamides as selective cyclooxygenase-2 inhibitors: enhancement of the selectivity by introduction of a fluorine atom and identification of a potent, highly selective, and orally active COX-2 inhibitor JTE-522 J. Med. Chem. 45 2002 1511
    • (2002) J. Med. Chem. , vol.45 , pp. 1511
    • Hashimoto, H.1    Imamura, K.2    Haruta, J.3    Wakitani, K.4
  • 21
    • 0034030366 scopus 로고    scopus 로고
    • N-[[(5-Methyl-3-phenylisoxazol-4-yl)-phenyl]sulfonyl]propanamide, sodium salt, parecoxib sodium: A potent and selective inhibitor of COX-2 for parenteral administration
    • J.J. Talley, S.R. Bertenshaw, D.L. Brown, J.S. Carter, M.J. Graneto, M.S. Kellogg, C.M. Koboldt, J. Yuan, Y.Y. Zhang, and K. Seibert N-[[(5-Methyl-3- phenylisoxazol-4-yl)-phenyl]sulfonyl]propanamide, sodium salt, parecoxib sodium: a potent and selective inhibitor of COX-2 for parenteral administration J. Med. Chem. 43 2000 1661
    • (2000) J. Med. Chem. , vol.43 , pp. 1661
    • Talley, J.J.1    Bertenshaw, S.R.2    Brown, D.L.3    Carter, J.S.4    Graneto, M.J.5    Kellogg, M.S.6    Koboldt, C.M.7    Yuan, J.8    Zhang, Y.Y.9    Seibert, K.10
  • 30
    • 16644377516 scopus 로고    scopus 로고
    • Market withdrawal of Vioxx: Is it time to rethink the use of COX-2 inhibitors?
    • E. Ortiz Market withdrawal of Vioxx: is it time to rethink the use of COX-2 inhibitors? J. Manag. Care Pharm. 10 2004 551
    • (2004) J. Manag. Care Pharm. , vol.10 , pp. 551
    • Ortiz, E.1
  • 31
    • 11244249628 scopus 로고    scopus 로고
    • Rofecoxib (Vioxx) voluntarily withdrawn from market
    • B. Sibbald Rofecoxib (Vioxx) voluntarily withdrawn from market Can. Med. Assoc. J. 171 2004 1027
    • (2004) Can. Med. Assoc. J. , vol.171 , pp. 1027
    • Sibbald, B.1
  • 32
    • 0001394390 scopus 로고
    • Preparation of phenyl thiohydantoins from some natural amino acids
    • P. Edman Preparation of phenyl thiohydantoins from some natural amino acids Acta Chem. Scand. 4 1950 277
    • (1950) Acta Chem. Scand. , vol.4 , pp. 277
    • Edman, P.1
  • 35
    • 3242735671 scopus 로고    scopus 로고
    • Structural approach for COX-2 inhibition
    • C. Michaux, and C. Charlier Structural approach for COX-2 inhibition Mini Rev. Med. Chem. 4 2004 603
    • (2004) Mini Rev. Med. Chem. , vol.4 , pp. 603
    • Michaux, C.1    Charlier, C.2
  • 40
    • 0343851682 scopus 로고    scopus 로고
    • Automated docking and molecular dynamics simulations of nimesulide in the cyclooxygenase active site of human prostaglandin-endoperoxide synthase-2 (COX-2)
    • R. Garcia-Nieto, C. Perez, and F. Gago Automated docking and molecular dynamics simulations of nimesulide in the cyclooxygenase active site of human prostaglandin-endoperoxide synthase-2 (COX-2) J. Comput. Aided Mol. Des. 14 2000 147
    • (2000) J. Comput. Aided Mol. Des. , vol.14 , pp. 147
    • Garcia-Nieto, R.1    Perez, C.2    Gago, F.3
  • 42
    • 0033594911 scopus 로고    scopus 로고
    • Nonsteroid drug selectivities for cyclo-oxygenase-1 rather than cyclo-oxygenase-2 are associated with human gastrointestinal toxicity: A full in vitro analysis
    • T.D. Warner, F. Giuliano, I. Vojnovic, A. Bukasa, J.A. Mitchell, and J.R. Vane Nonsteroid drug selectivities for cyclo-oxygenase-1 rather than cyclo-oxygenase-2 are associated with human gastrointestinal toxicity: a full in vitro analysis Proc. Natl. Acad. Sci. U.S.A. 96 1999 7563
    • (1999) Proc. Natl. Acad. Sci. U.S.A. , vol.96 , pp. 7563
    • Warner, T.D.1    Giuliano, F.2    Vojnovic, I.3    Bukasa, A.4    Mitchell, J.A.5    Vane, J.R.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.