Stereoselectivity of a potent calcium antagonist, 1-benzyl-3-pyrrolidinyl methyl 2, 6-dimethyl-4-(m-nitrophenyl)-1, 4-dihydropyridine-3, 5-dicarboxylate

…, H Arima, T Kojima, Y Isomura, M Okada…

Index: Tamazawa, Kazuharu; Arima, Hideki; Koijma, Tadao; Isomura, Yasuo; Okada, Minoru; et al. Journal of Medicinal Chemistry, 1986 , vol. 29, # 12 p. 2504 - 2511

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Citation Number: 95

Abstract

(R)-l-benzyl-3-pyrrolidinol (2a or 2b).[3H] Nitrendipine binding affinity and coronary vasodilating activity of these compounds were evaluated. The absolute configuration of the most potent enantiomer (3a) with the longest duration was unequivocally determined to be (S)-1, 4-dihydropyridine-C4 and (S)-pyrrolidine-C3 (S, S) by X-ray crystallographic study on 3a. HBr as well as 3a. HCl. The configuration of la corresponds to R, and the other ...