Abstract
The tautomeric preference of rigid imidazole derivatives has been analyzed theoretically from molecular orbital calculations ab initio. The present results indicate that the reduced potencies exhibited by imidazolylphenylene analogues of cimetidine and metiamide at the H2-receptor are consistent with those hypotheses that defined the N3-H tautomer of the monocation as the only recognizable species in this class of histamine H2-ligand. However, our results suggest that the 4-methylimidazolylphenylene analogue of cimetidine could be an effective histamine H3-antagonist.
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