Studies on Antiulcer Agents. IV. Synthesis and Antiulcer Activity of Phenylpropanol Derivatives

Abstract

It was found that (±) ethyl 2-[2-(3-hydroxypropyl)-4-oxocyclohexylidene]-propionate (1), (±) ethyl 2-[2-(3-hydroxypropyl)-4, 5-dimethoxyphenyl] propionate (2), (±) 3-[2-(3-hydroxypropyl)-4, 5-dimethoxyphenyl]-2-butanone (3) and (±) 2-[2-(3-hyroxypropyl)-4-methoxy-5-(2-piperidinoethoxy) phenyl] cyclopentanone (4) had potent antiulcer activities. In order to study structure-activity relationships, (±) 3-[(3-hydroxypropyl) phenoxy]-2-butanone derivatives (5, 6) were synthesized and tested for antiulcer activities. Among them, (±) 3-[2-(3-hydroxypropyl)-4-methoxy-5-[3-(4-methylpiperidino) propoxy] phenoxy]-2-butanone·3/2 oxalate (6k) was selected as a preferred antiulcer agent.