Structure-activity relationships for 2-substituted imidazoles as alpha 2-adrenoceptor antagonists.

doi:10.1021/JM00348A012

Paper

Structure-activity relationships for 2-substituted imidazoles as alpha 2-adrenoceptor antagonists.

Published Jun 1, 1982 · J. Caroon, R. D. Clark, A. Kluge

Journal of medicinal chemistry

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26

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0

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Abstract

Several 2-[(1,4-benzodioxan-2-yl)alkyl]imidazoles were prepared and evaluated for their blocking activity and relative selectivity on presynaptic (alpha 2) and postsynaptic (alpha 1) receptors in the isolated rat vas deferens. 1-Ethyl-2-[(1,4-benzodioxan 2-yl)methyl]imidazole (13) was the most selective alpha 2-adrenoceptor antagonist of the series and was, for practical purposes, devoid of alpha 1-adrenoceptor antagonist activity. The lipophilicity of 13 (log D = 2.31) indicated that it would have an excellent chance to enter the central nervous system. Compound 13 was selected for clinical evaluation as an antidepressant agent.

In Vitro Study

Study Snapshot

1-Ethyl-2-[(1,4-benzodioxan-2-yl)methyl]imidazole (13) is a highly selective alpha 2-adrenoceptor antagonist with potential as an antidepressant agent due to its excellent lipophilicity and central nervous system penetration.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Structure-activity relationships for 2-substituted imidazoles as alpha 2-adrenoceptor antagonists.

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