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
收藏
页码：140 / 149
页数：10
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