[Synthesis and antiulcer effects of 5-hydroxy-4-[2-substituted-(E)-ethenyl]-2(5H)-furanone. (1)].
gamma-Hydroxybutenolides possessing conjugated substituents at the beta-position and their related compounds have been synthesized by the previously reported procedure with minor modifications and their antiulcer activities have been examined in the HCl-ethanol induced ulcer model often used for the evaluation of gastric mucosal protective factor enhancing effect. The compound A-1 5-hydroxy-4-[2-(2,6,6-trimethyl-1-cycohexenyl-1-yl)-(E)-ethenyl]-2 (5H)-furanone showed a pronounced effect at a low dosage of 5 mg/kg p.o. and some analogues compounds also exhibited potent inhibitory activity as compared with the reference drugs. The relationship between the structure of gamma-hydroxybutenolides and the antiulcer effect has been also examined and then the 5-hydroxyl group has been found to be essentially functional one to have antiulcer activity.
Tamai
Y
Y
Kuraray Co., Ltd., Nakajhochou Niigata, Japan.
Torihara
M
M
Kido
Y
Y
Yamahara
J
J
Motizuki
M
M
Ito
M
M
Katsuta
Y
Y
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D000897:Anti-Ulcer Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D005753:Gastric Mucosa / Q000187:drug effects*; D051381:Rats; D012176:Retinoids / Q000138:chemical synthesis / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014456:Ulcer / Q000139:chemically induced / Q000188:drug therapy
D000897:Anti-Ulcer Agents; D012176:Retinoids; C077240:KYN 54; D015107:4-Butyrolactone