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.