[Studies on antiulcer agents. IV. Synthesis and antiulcer activity of phenylpropanol derivatives].
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-hydroxypropyl)-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.
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* / Q000737:chemistry / Q000494:pharmacology; D001559:Benzhydryl Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D017207:Rats, Sprague-Dawley; D013329:Structure-Activity Relationship
D000897:Anti-Ulcer Agents; D001559:Benzhydryl Compounds; D000433:1-Propanol