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

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.