C-(β-D-glucopyranosyl) heterocycles as potential glycogen phosphorylase inhibitors

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Abstract

Per-O-acetylated and -benzoylated β-D-glucopyranosyl cyanides were transformed into the corresponding 5-(β-D-glucopyranosyl)tetrazoles, 2-(β-D-glucopyranosyl)benzothiazoles, and, via the benzoylated C-(β-D-glucopyranosyl) ethyl thioformimidate, 2-(β -D-glucopyranosyl)-benzimidazoles. Acylation of the tetrazoles, either by acetic or trifluoroacetic anhydride, gave 5-(β-D-glucopyranosyl)-2-methyl- and -2-trifluoromethyl-1,3,4-oxadiazoles, respectively. Removal of the protecting groups furnished new inhibitors of glycogen phosphorylase exhibiting inhibitor constants in the micromolar range.

Original languageEnglish
Pages (from-to)140-149
Number of pages10
JournalArkivoc
Volume2004
Issue number7
Publication statusPublished - Jan 1 2004

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Keywords

  • Benzimidazole, 1,3,4-oxadiazole
  • Benzothiazole
  • C-(β-D-glucopyranosyl) heterocycles
  • Glycogen phosphorylase
  • Inhibitors
  • Tetrazole

ASJC Scopus subject areas

  • Organic Chemistry

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