Antiulcer agents. III. Synthesis and antiulcer activity of N-[3-(3- piperidinomethylphenoxy)propyl]pentacyclo[4.2.0.02,5.03,8.04,7]- octane carboxamides and related compounds

Article abstract of DOI:10.1248/cpb.41.1760

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 H₂-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.

Full text of DOI:10.1248/cpb.41.1760

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