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

Abstract

Abstract 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.