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

Heterocyclic communications

article

Stanislava Vladimirova¹  Atanas Bijev¹ 

[1]Department of Organic Synthesis and Fuels, University of Chemical Technology and Metallurgy

关键词: COX-2 inhibitors;    Paal-Knorr cyclization;    pyrroles;    synthesis;   

DOI  :  10.1515/hc-2014-0022

学科分类：内科医学

来源: De Gruyter

【 摘 要 】

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.

【 授权许可】

CC BY|CC BY-NC-ND