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

被引：60

作者：

Hadady, Z ^{[1
]}

Tóth, M ^{[1
]}

Somsák, L ^{[1
]}

机构：

[1] Univ Debrecen, Dept Organ Chem, POB 20, H-4010 Debrecen, Hungary

来源：

ARKIVOC | 2004年

关键词：

C-(beta-D-glucopyranosyl) heterocycles; tetrazole; benzothiazole; benzimidazole; 1,3,4-oxadiazole; inhibitors; glycogen phosphorylase;

D O I：

10.3998/ark.5550190.0005.711

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Per-O-acetylated and - benzoylated beta-D-glucopyranosyl cyanides were transformed into the corresponding 5-(beta-D-glucopyranosyl) tetrazoles, 2-(beta-D-glucopyranosyl) benzothiazoles, and, via the benzoylated C-(beta-D-glucopyranosyl) ethyl thioformimidate, 2-(beta-D-glucopyranosyl)benzimidazoles. Acylation of the tetrazoles, either by acetic or trifluoroacetic anhydride, gave 5(beta-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.

引用

页码：140 / 149

页数：10