Synthesis and Activity of Optical Isomers of Nipradilol

MASAMI SHIRATSUCHI; KIYOSHI KAWAMURA; TOSHIHIRO AKASHI; HIROSHI ISHIHAMA; MASAKI NAKAMURA; FUMIO TAKENAKA

doi:10.1248/cpb.35.3691

MASAMI SHIRATSUCHI, KIYOSHI KAWAMURA, TOSHIHIRO AKASHI, HIROSHI ISHIHAMA, MASAKI NAKAMURA, FUMIO TAKENAKA

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Keywords: nipradilol, synthesis, optical isomer, β-blocking activity, α-blocking activity, vasodilating activity, benzopyran

JOURNAL FREE ACCESS

1987 Volume 35 Issue 9 Pages 3691-3698

DOI https://doi.org/10.1248/cpb.35.3691

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Abstract

Four optical isomers of nipradilol (NIP) were prepared from (3R) -or (3S) -3, 4-dihydro-8-hydroxy-3-nitroxy-2H-1-benzopyran by glycidylation and amination, and evaluated for β-blocking and vasodilating activities. The order of potency of β-blocking activity was S, R-NIP>> S, S-NIP > R, R-NIP>> R, S-NIP. As regards vasodilating activity, S, R-NIP and R, R-NIP were more potent than S, S-NIP and R, S-NIP.

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