An access to new N-pyrrolylcarboxylic acids as potential COX-2 inhibitors via Paal-Knorr cyclization

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2014-01-01
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Twenty new N-pyrrolylcarboxylic acids were designed to assume the architecture of contemporary selective COX-2 inhibitors as potential anti-inflammatory agents. The targeted products were synthesized in 70-82% yields by Paal-Knorr cyclization of a set of eight amino acids, acting as primary amines, and four 1,4-dicarbonyl compounds. The latter substrates were prepared by C-alkylation of three commercially available β-dicarbonyl compounds with two ω-bromoacetophenones and used in situ. These compounds inhibit carrageenin-induced rat paw edema and show analgesic activity.
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