Synthesis and Pharmacological Effects of Optically Active 2-[4-(4-BenzhydryH-piperazinyl)phenyl]-ethyl Methyl l,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate Hydrochloride

Abstract

Optically active 2-[4-(4-benzhydryl-l-piperazinyl)phenyl]ethyl methyl l,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate [(*S)-(+)-l and (/?)-(—)-l] hydrochlorides were synthesized with high optical purities from (/?)-(—)- and (S)-(+)-l,4-dihydro-5-methoxycarbonyl-2,6-dimethyl“4-(3-nitrophenyl)-3-pyridinecarboxylic acids [(/?)-(—)-6 and (£)-(+)-6], which are available from (±)-6 by optical resolution using quinidine and cinchonidine, respectively. From pharmacological investigations of (£)-(+)-! and (/?)-(—)-l such as the antihypertensive effect on spontaneously hypertensive rats and inhibition of [3H]nimodipine binding to rat cardiac membrane homogenate, the active form of 1 was defined to be the (4S)-(+ Venantiomer of 1. © 1991, The Pharmaceutical Society of Japan. All rights reserved.