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.

New chiral methyloxyiminomethyl(MOIM) beta-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 beta-adrenergic blocking agents

BRESCHI, MARIA CRISTINA;CHIELLINI, GRAZIA;MACCHIA, MARCO;MANERA, CLEMENTINA;
1996

Abstract

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.
Balsamo, A; Breschi, MARIA CRISTINA; Chiellini, Grazia; Macchia, B; Macchia, Marco; Manera, Clementina; Sacca, P; Scatizzi, R.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/205769
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