Synthesis of C-β-D-glucopyranosyl derivatives of some fused azoles for the inhibition of glycogen phosphorylase

被引：7
作者：
Szennyes, Eszter [1 ]
Bokor, Eva [1 ]
Docsa, Tibor [2 ]
Sipos, Adam [2 ]
Somsak, Laszlo [1 ]
机构：
[1] Univ Debrecen, Dept Organ Chem, POB 400, H-4002 Debrecen, Hungary
[2] Univ Debrecen, Fac Med, Dept Med Chem, Egyet Ter 1, H-4032 Debrecen, Hungary
来源：
CARBOHYDRATE RESEARCH | 2019年 / 472卷
关键词：
C-glycosyl heterocycle; Fused azole; Imidazole; Inhibitor; Glycogen phosphorylase; GLUCOSE ANALOG INHIBITORS; BINDING; NUCLEOSIDES; IMIDAZOLES; REVEAL; MUSCLE;
D O I：
10.1016/j.carres.2018.11.003
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Annulated C-beta-D-glucopyranosyl heterocycles were synthesized and tested as inhibitors of glycogen phosphorylase. 2-(beta-D-Glucopyranosyl)-1H-imidazo[4,5-b] pyridine was formed by ring-closure of O-perbenzoylated C-beta-D-glucopyranosyl formic acid with 2,3-diaminopyridine in the presence of triphenylphosphite. Cyclisations of bromomethyl 2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl ketone with a set of 2-aminoheterocycles resulted in constitutionally reversed C-beta-D-glucopyranosyl imidazoles fused by pyridine, pyrimidine, thiazole, 1,3,4-thiadiazole, benzothiazole and benzimidazole. O-Debenzoylation of the above compounds was effected by standard transesterification to get the test compounds. The 1H-imidazo[4,5-b] pyridine proved to be a low micromolar inhibitor (K-i = 21.1 mu M) of rabbit muscle glycogen phosphorylase b, while the other heterocycles displayed weak or no inhibition against the same enzyme.
引用
收藏
页码：33 / 41
页数：9
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