Molecular Conformations of Aminophenylimidazoles Exhibiting Antiulcer Activities

概要

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To experimentally clarify a possible stereostructure-activity relationship proposed for H_2-receptor antagonists, three 5-aminophenylimidazoles (1,2 and 3), in which respective amino groups are located on the ortho, meta and para positions of the benzene ring, were synthesized and examined for their conformational characteristics using X-ray diffraction and proton nuclear magnetic resonance ( ^1H-NMR) methods, and for antiulcer activities on rats and H_2-receptor antagonist activities in guinea pig. The ortho isomer 1,which preferentially formed an intramolecular N-H (amino)…N (imidazole) hydrogen bond, showed the highest antiulcer activity with half the efficacy of cimetidine. On the other hand, none of 1,2 and 3 showed significant H_2-receptor antagonist activity. Based on these results, the conformational characteristic for the exhibition of antiulcer activity has been discussed.
社団法人日本薬学会の論文
1990-07-25