Antiulcer agents. II. Synthesis and gastric acid antisecretory activity of N-[3-(3-(piperidinomethyl)phenoxy)propyl]-4-(1-methyl-1H- tetrazol-5-ylthio)butanamide and related compounds.
N-[3-(3-(Piperidinomethyl)phenoxy)propyl]butanamides having a 1-methyl-1H-tetrazol-5-ylthio moiety as a pharmacophore and related compounds were prepared and tested for their antisecretory activity against histamine-induced gastric acid secretion in conscious rats with gastric fistulas. Most of the compounds showed antisecretory activity. Among them, N-[3-(3-(piperidinomethyl)phenoxy)propyl]-4-(1-methyl-1 H-tetrazol-5-ylthio)butanamide (5f) was found to posses the most potent activity, and a possibility of isosteric replacement of the methoxycarbonyl group with 1-methyl-1H-tetrazol-5-yl group was indicated. The structure-activity relationships are also discussed.
Institute of Scientific and Industrial Research, Osaka University, Japan.
I
I
Ueda
K
K
Ishii
K
K
Sinozaki
M
M
Seiki
M
M
Hatanaka
D000818:Animals; D000897:Anti-Ulcer Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D005744:Gastric Acid / Q000378:metabolism; D010880:Piperidines / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D013329:Structure-Activity Relationship; D013777:Tetrazoles / Q000138:chemical synthesis* / Q000494:pharmacology
D000897:Anti-Ulcer Agents; D010880:Piperidines; D013777:Tetrazoles; C071489:N-(3-(3-(piperidinomethyl)phenoxy)propyl)-4-(1-methyl-1H-tetrazol-5-ylthio)butanamide