, Volume 22, Issue 7, pp 3510-3517
Date: 25 Nov 2012

Synthesis and investigation of anti-inflammatory activity of novel nitric oxide donating hybrid drugs

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Abstract

A small library of nitric oxide donating groups, 4-acetamidophenyl-2-[{2-(nitrooxy)ethyl}(phenyl) amino]benzoate (5a–e) possessing a variety of substituents (–H, –NO2, –CH3, –acetamidophenyl, –SO2NH2) attached to the fourth position of phenyl ring were synthesized and evaluated for anti-inflammatory, analgesic and ulcerogenic potential. Structure–activity relationship data showed that the 2-phenylaminobenzoic acid skeleton is required for selective COX-2 inhibition. Among all compounds 4-acetamidophenyl-2-[{2-(nitrooxy)ethyl}(phenyl)amino]benzoate (5a) has shown potent anti-inflammatory activity while 4-acetamidophenyl-2-[{4-{(4-acetamidophenoxy)carbonyl} phenyl}{2-(nitrooxy)ethyl}amino]benzoate (5d) has shown potent analgesic activity compared to standard drug diclofenac.