NEW CHIRAL METHYLOXYIMINOMETHYL(MOIM) BETA-ADRENERGIC ANTAGONISTS - -HYDROXYPROPYLIDENE](P-CHLOROPHENYLMETHYLOXY)AMINE AND -HYDROXYPROPYLIDENE](P-CHLOROPHENYLMETHYLOXY)AMINE AS PROBES FOR DETERMINING ENANTIOMERIC SPECIFICITY IN THE CLASS OF MOIM-TYPE BETA-ADRENERGIC BLOCKING-AGENTS

The chiral (S)- and 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 pre cursors of known absolute configuration by procedures which had no eff ect on the configuration of the asymmetric carbon. Compounds (S)-1a,b and (R)-1a,b were tested for their beta-adrenergic properties by radio ligand binding experiments and functional tests on isolated preparatio ns. The biopharmacological results show that compounds (S)-1a,b, in wh ich the geometry of the chiral carbon adjacent to the hydroxyl group r esembles that of natural catecholamines with the R configuration, inte racted better with beta-receptors, even if the stereochemical selectiv ity among enantiomeric pairs is not particularly marked.