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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.

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, Sinhgad Institute of Pharmacy, Narhe, Pune, 411 041, Maharashtra, India

    Shailesh L. Chandak, Amol S. Bansode, Prashant R. Murumkar, Monika G. Shinde & Kailash G. Bothara

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  1. Shailesh L. Chandak
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  2. Amol S. Bansode
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  3. Prashant R. Murumkar
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  4. Monika G. Shinde
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  5. Kailash G. Bothara
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Correspondence to Kailash G. Bothara.

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Chandak, S.L., Bansode, A.S., Murumkar, P.R. et al. Synthesis and investigation of anti-inflammatory activity of novel nitric oxide donating hybrid drugs. Med Chem Res 22, 3510–3517 (2013). https://doi.org/10.1007/s00044-012-0345-y

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  • DOI: https://doi.org/10.1007/s00044-012-0345-y

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