Studies on Antiulcer Agents. III. 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) and (±) 3-[2-(3-hydroxypropyl)-4, 5-dimethoxyphenyl]-2-butanone (3) had excellent antiulcer activities. In order to study structure-activity relationships, (±) 2-[(3-hydroxypropyl) phenyl] cyclopentanone derivatives (4, 5) and (±) 2-[(3-hydroxypropyl) phenyl] cyclopentanol derivatives (6, 7) were synthesized and tested for antiulcer activities. As a result, (±) 2-[2-(3-hydroxypropyl)-4-methoxy-5-(2-piperidinoethoxy) phenyl] cyclopentanone (5k) exhibited potent antiulcer activities.