Polar substitutions in the benzenesulfonamide ring of celecoxib afford a potent 1,5-diarylpyrazole class of COX-2 inhibitors

Bioorganic & Medicinal Chemistry Letters
2004.0

Abstract

Several chemical modifications in the N(1)-benzenesulfonamide ring of celecoxib are presented. The series with a hydroxymethyl group adjacent to the sulfonamide was found to be the most potent modification that yielded many compounds selectively active against COX-2 enzyme in vitro.

Knowledge Graph

Similar Paper

Polar substitutions in the benzenesulfonamide ring of celecoxib afford a potent 1,5-diarylpyrazole class of COX-2 inhibitors
Bioorganic & Medicinal Chemistry Letters 2004.0
New Celecoxib Derivatives as Anti-Inflammatory Agents
Journal of Medicinal Chemistry 2008.0
Synthesis and Biological Evaluation of the 1,5-Diarylpyrazole Class of Cyclooxygenase-2 Inhibitors:  Identification of 4-[5-(4-Methylphenyl)-3- (trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (SC-58635, Celecoxib)
Journal of Medicinal Chemistry 1997.0
Selective COX-2 inhibitors. Part 1: Synthesis and biological evaluation of phenylazobenzenesulfonamides
Bioorganic & Medicinal Chemistry Letters 2006.0
Methanesulfonamide group at position-4 of the C-5-phenyl ring of 1,5-diarylpyrazole affords a potent class of cyclooxygenase-2 (COX-2) inhibitors
Bioorganic & Medicinal Chemistry Letters 2004.0
Synthesis of novel celecoxib analogues by bioisosteric replacement of sulfonamide as potent anti-inflammatory agents and cyclooxygenase inhibitors
Bioorganic & Medicinal Chemistry 2013.0
Selective COX-2 inhibitors. Part 2: Synthesis and biological evaluation of 4-benzylideneamino- and 4-phenyliminomethyl-benzenesulfonamides
Bioorganic & Medicinal Chemistry 2008.0
Synthesis of N-benzenesulfonamide-1H-pyrazoles bearing arylsulfonyl moiety: Novel celecoxib analogs as potent anti-inflammatory agents
European Journal of Medicinal Chemistry 2014.0
Synthesis and Cyclooxygenase-2 Inhibiting Property of 1,5-Diarylpyrazoles with Substituted Benzenesulfonamide Moiety as Pharmacophore:  Preparation of Sodium Salt for Injectable Formulation<sup>†</sup>
Journal of Medicinal Chemistry 2003.0
Synthesis and activity of sulfonamide-substituted 4,5-diaryl thiazoles as selective cyclooxygenase-2 inhibitors
Bioorganic &amp; Medicinal Chemistry Letters 1999.0