NOVEL AND CHIRAL HANTZSCH-TYPE 1, 4-DIHYDROPYRIDINES HAVING A p-TOLYLSULFINYL GROUP. SYNTHESIS AND BIOLOGICAL ACTIVITIES AS CALCIUM CHANNEL ANTAGONISTS

Kazuyuki MIYASHITA; Masahiro NISHIMOTO; Tetsuya ISHINO; Satoshi OBIKA; Takeshi IMANISHI

doi:10.1248/cpb.43.711

Kazuyuki MIYASHITA, Masahiro NISHIMOTO, Tetsuya ISHINO, Satoshi OBIKA, Takeshi IMANISHI

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Keywords: Hantzsch-ester, 1, 4-dihydropyridine, p-tolylsulfinyl group, synthesis, optically active form, calcium channel antagonist

JOURNAL FREE ACCESS

1995 Volume 43 Issue 4 Pages 711-713

DOI https://doi.org/10.1248/cpb.43.711

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Abstract

Both C-4 stereoisomers of novel Hantzch-type 4-aryl- and 4-methyl-1, 4-dihydropyridines 3 having a p-tolylsulfinyl group at C-5 were efficiently synthesized in optically pure forms starting from the α-sulfinyl enones 6 which could be easily obtained from (-)-menthyl (S)-p-tolylsulfinate (4). The stereochemistry at C-4 was found to be largely responsible for the biological activities as calcium channel antagonists of these compounds.

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