[Studies on antiulcer agents. II. Synthesis and antiulcer activity of phenylpropanol derivatives].
It was found that gamma-irigermanal, obtained from the methanol extract of root of Iris germanica, exhibited a potent antiulcer activity. Therefore, this compound was selected as a lead-compound, and related compounds were synthesized and tested for antiulcer activities. It was found that (+/-) ethyl 2-[2-(3-hydroxypropyl)-4-oxocyclohexylidene]- propionate (1) had excellent antiulcer activities. Then phenylpropanol derivatives, obtained by changing from cyclohexane ring of 1 to benzene ring, were synthesized and tested for antiulcer activities in order to study structure activity relationships. As a result, (+/-) ethyl 2-[2-(3-hydroxypropyl)-4,5-dimethoxy-phenyl]propionate (2b) and (+/-) 3-[2-(3-hydroxypropyl)-4,5-dimethoxyphenyl]-2-butanone (5) were shown to have antiulcer activities.
Muto
Y
Y
Central Research Laboratories, Zeria Pharmaceutical Co., Ltd., Saitama, Japan.
Ichikawa
H
H
Seiki
M
M
Shirataki
Y
Y
Yokoe
I
I
Komatsu
M
M
D000433:1-Propanol / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D000897:Anti-Ulcer Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D020005:Propanols; D051381:Rats; D017207:Rats, Sprague-Dawley; D013276:Stomach Ulcer / Q000188:drug therapy; D013329:Structure-Activity Relationship
D000897:Anti-Ulcer Agents; D020005:Propanols; D000433:1-Propanol