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A simple and efficient one-pot novel synthesis of pyrazolo[3,4-b][1,8]naphthyridine and pyrazolo[3,4-d]pyrimido[1,2-a]pyrimidine derivatives as anti-inflammatory agents

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Abstract

An efficient one-pot synthesis of novel pyrazolo[3,4-b][1,8]naphthyridine and pyrazolo[3,4-d]pyrimido[1,2-a]pyrimidine derivatives has been investigated from the reaction of 2-amino (pyrimidine or pyridine), aromatic aldehydes and 3-methyl-1-phenyl-2-pyrazolin-5-one. All synthesized compounds were evaluated for in vivo anti-inflammatory activity using carrageenan-induced rat paw edema assay. Compounds 4a, 4e, 4g, 5a, 5b (80%) and 5c (86%) showed good to excellent results when compared with the anti-inflammatory active standard drug diclofenac Na (93%). On the basis of the structure–activity relationship, the anti-inflammatory activity of pyrazolo[3,4-d]pyrimido[1,2-a]pyrimidine derivatives has been found to be much better than pyrazolo[3,4-b][1,8]naphthyridine derivatives.

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Authors and Affiliations

  1. Department of Agrochemicals and Pest Management, Shivaji University, Kolhapur, Maharashtra, 416004, India

    Priyanka T. Patil, Poojali P. Warekar & Kirti T. Patil

  2. Medicinal Chemistry Research Laboratory, Department of Chemistry, Shivaji University, Kolhapur, Maharashtra, 416004, India

    Santosh S. Undare, D. K. Jamale, S. S. Vibhute, N. J. Valekar, Govind B. Kolekar, Madhukar B. Deshmukh & Prashant. V. Anbhule

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  1. Priyanka T. Patil
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Correspondence to Prashant. V. Anbhule.

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Patil, P.T., Warekar, P.P., Patil, K.T. et al. A simple and efficient one-pot novel synthesis of pyrazolo[3,4-b][1,8]naphthyridine and pyrazolo[3,4-d]pyrimido[1,2-a]pyrimidine derivatives as anti-inflammatory agents. Res Chem Intermed 44, 1119–1130 (2018). https://doi.org/10.1007/s11164-017-3155-5

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