1-Toluene-sulfonyl-3-[(3′-hydroxy-5′-substituted)-γ-butyrolactone]-indoles: Synthesis, COX-2 inhibition and anti-cancer activities

Indoles carrying a cyclic ester (γ-butyrolactone) at C-3 position have been synthesized by the allylation of 3-indoleglyoxylate followed by iodocyclisation and the nucleophilic replacement of the iodo-group. Screening of these molecules for COX-2 inhibition and anti-cancer activities has identified compounds 10 and 11 as highly potent and selective for COX-2 as well as showing remarkable anti-cancer activities (better than that of indomethacin).

Graphical abstractAllylation-iodocyclisation and nucleophilic replacement reactions on 3-indoleglyoxylate, have provided butyrolactone substituted indoles with high COX-2 inhibitory activities and remarkable anti-cancer activities.Figure optionsDownload full-size imageDownload as PowerPoint slide