Synthesis and biological evaluation of ketorolac analogs

Ketorolac analogs were synthesized and biologically evaluated. For the preparation of the N-methylpyrrole Rol 14-1907, and the furan Rol 13-8905, a hydroxyethyl-assisted regioselective benzoylation gave intermediates (4) and (12), and subsequently a key copper-mediated ring closure gave entry to the required bicyclic compounds (7) and (15). Ro113-8905 and the thiophene Ro101-8244 significantly inhibited both the writhing response and edema formation in rat, but were less potent than Ketorolac.