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

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

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 ste...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1995/04/15, Vol.43(4), pp.711-713
Hauptverfasser: MIYASHITA, Kazuyuki, NISHIMOTO, Masahiro, ISHINO, Tetsuya, OBIKA, Satoshi, IMANISHI, Takeshi
Format: Artikel
Sprache:eng
Schlagworte:
1, 4-dihydropyridine
calcium channel antagonist
Chemistry
Exact sciences and technology
Hantzsch-ester
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
optically active form
Organic chemistry
p-tolylsulfinyl group
Preparations and properties
synthesis
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Beschreibung
Zusammenfassung: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.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.43.711