New chiral methyloxyiminomethyl (MOIM) β-adrenergic antagonists. (S)- and (R)-N-[3-(alkylamino)-2-hydroxypropylidene](p-chlorophenylmethyloxy)amines as probes for determining enantiomeric specificity in the class of MOIM-type β-adrenergic blocking agents

Article abstract of DOI:10.1016/0223-5234(96)89135-5

The chiral (S)- and (R)-N-[3-(isopropylamino)-2-hydroxypropylidene](p-chlorophenylmethyloxy)amines ((S)-1a and (R)-1a) and their corresponding N-tert-butyl-substituted analogs ((S)-1b and (R)-1b) were synthesized from optically active precursors of known absolute configuration by procedures which had no effect on the configuration of the asymmetric carbon. Compounds (S)-1a,b and (R)-1a,b were tested for their β-adrenergic properties by radioligand binding experiments and functional tests on isolated preparations. The biopharmacological results show that compounds (S)-1a,b, in which the geometry of the chiral carbon adjacent to the hydroxyl group resembles that of natural catecholamines with the R configuration, interacted better with β-receptors, even if the stereochemical selectivity among enantiomeric pairs is not particularly marked.