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.
D000317:Adrenergic alpha-Antagonists / Q000494:pharmacology*; D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D005021:Ethylamines / Q000138:chemical synthesis / Q000494:pharmacology; D066298:In Vitro Techniques; D007536:Isomerism; D008297:Male; D009119:Muscle Contraction / Q000187:drug effects; D051381:Rats; D014649:Vas Deferens / Q000187:drug effects
D000317:Adrenergic alpha-Antagonists; D005021:Ethylamines