STUDIES ON ANTIULCER AGENTS .2. SYNTHESIS AND ANTIULCER ACTIVITY OF PHENYLPROPANOL DERIVATIVES

It was found that gamma-irigermanal, obtained from the methanol extrac t of root of Iris germanica, exhibited a potent antiulcer activity.(1) ) Therefore, this compound was selected as a lead-compound, and relate d compounds were synthesized and tested for antiulcer activities. It w as found that (+/-) ethyl (3-hydroxypropyl)-4-oxocyclohexylidene]-prop ionate (1) had excellent antiulcer activities.(3)) Then phenylpropanol derivatives, obtained by changing from cyclohexane ring of 1 to benze ne ring, were synthesized and tested for antiulcer activities in order to study structure-activity relationships. As a result, (+/-) ethyl 2 -(3-hydroxypropyl)-4,5-dimethoxyphenyl]propionate (2b) and (+/-) -(3-h ydroxypropyl)-4,5-dimethoxyphenyl]-2-butanone (5) were shown to have a ntiulcer activities.