1-(4-Methane(amino)sulfonylphenyl)-3-(4-substituted-phenyl)-5-(4-trifluoromethylphenyl)-1H-2-pyrazolines/pyrazoles as potential anti-inflammatory agents

• Two groups of 2-pyrazoline and pyrazole derivatives were designed and synthesized.
• All the compounds were more selective COX-2 inhibitors than aspirin and ibuprofen.
• 14g and 14i exhibited AI activity 4-fold more potent than aspirin, 2-fold more potent than ibuprofen.
• 14g and 14i could be used as a lead compound for developing new anti-inflammatory agents.

2-Pyrazolins 14a–l and pyrazoles 15a–l were designed as celecoxib analogs for the evaluation of their in vitro COX-1/COX-2 inhibitory activity and the in vivo anti-inflammatory activity. Compounds 14i, 15a, 15d and 15f were the most COX-2 selective derivatives (S.I. = 5.93, 6.08, 5.03 and 5.27 respectively) while the pyrazoline derivatives 14g and 14i exhibited the highest AI activity (ED50 = 190.5 and 160.1 μmol/kg po, respectively).

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