β-Adrenergic blocking agents. 20. (3-Hydroxyprop-1-enyl)-substituted 1-(aryloxy)-3-(alkylamino)propan-2-ols

Article abstract of DOI:10.1021/jm00184a011

The synthesis of a series (3-hydroxyprop-1-enyl)-substituted 1-(aryloxy)-3-(alkylamino)propan-2-ols is described. These compounds were investigated for their β-adrenoreceptor blocking properties and their selectivity of action. Among the o-(hydroxypropenyl)-substituted derivatives the authors have found some potent noncardioselective β-adrenoreceptor blocking agents which have a greater blocking action on the β₂ receptor, thus resembling propanolol. The p-(hydroxypropenyl)-substituted analogues were generally less potent and tended to be cardioselective. The structure-activity relationships are discussed in the light of the hypothesis that the cardioselectivity of p-amido-substituted (aryloxy)propanolamines is attributable, in part, to binding of the amide group to some additional site on the β receptor; these findings argue against a similar interaction for the allylic hydroxyl group.