Antiulcer Agents. III. Synthesis and Antiulcer Activity of N-[3-(3-Piperidinomethylphenoxy)propyl]pentacyclo[4.2.0.0^<2,5>.0^<3,8>.0^<4,7>]-octane Carboxamides and Related Compounds

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The synthesis and antiulcer activity of highly strained cage compounds such as pentacyclo[4.2.0.0^<2,5>.0^<3,8>.0^<4,7>]-octane (cubane), pentacyclo[4.3.0.0^<2,5>.0^<3,8>.0^<4,7>]nonane (homocubane) and pentacyclo[5.3.0.0^<2,4>.0^<3,6>.0<5,8>]decane are described. Of the compounds obtained, N-[3-(3-piperidinomethylphenoxy)propyl]-4-piperidinocarbonylpentacyclo[4.2.0.0^<2,5>.0^<3,8>.0<4,7>]octane carboxamide (26a) and N-[3'-(3'-piperidinomethylphenoxy)propyl]-1-bromo-9,9-ethylenedioxypentacyclo[4.3.0.0^<2,5>.0^<3,8>.0^<4,7>]nonane]-4-carboxamide (26q) showed more potent antiulcer activity with very good cytoprotective ability in the HCl・ethanol-treated rat model. Compounds 26a and 26q exhibited H_2-receptor antagonist potency (in vitro) comparable to that of ranitidine, but did not inhibit histamine-stimulated acid secretion (in vivo) in the gastric fistula rat model, when orally administered in the dose range at which antiulcer and cytoprotective activities were seen. The structure-activity relationships are discussed.
社団法人日本薬学会の論文
1993-10-15