Synthesis and alpha-adrenolytic activity of chiral beta-haloethylamines

Several series of N,N-diaralkyl- and N-aryloxyalkyl-N-aralkyl-beta-haloethylamines were synthesized containing centers of chirality in the aralkyl substituent and in the beta-haloethyl moiety to study the stereoselectivity of alpha-adrenolytic activity of the beta-haloethylamines. These compounds were synthesized from starting materials of known absolute configuration via synthetic schemes that did not alter the stereochemical integrity of the chiral centers. Evaluation of the alpha-adrenolytic activities of these beta-haloethylamines on rat vas deferens indicated a variable degree of stereoselectivity of adrenergic blockade, which is interpreted in terms of drug-receptor interactions.