Synthesis of monofluorinated isofagomine analogues and evaluation as glycosidase inhibitors

被引：15

作者：

Yang, Yi ^{[1
]}

Zheng, Feng ^{[1
]}

Bols, Mikael ^{[2
]}

Marinescu, Lavinia G. ^{[2
]}

Qing, Feng-Ling ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

[2] Univ Copenhagen, Dept Chem, DK-1168 Copenhagen, Denmark

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2011年 / 132卷 / 10期

基金：

中国国家自然科学基金;

关键词：

Iminosugar; Glycosidase inhibitor; Fluorinated compounds; C-F BOND; ASYMMETRIC-SYNTHESIS; FLUORINATED ANALOGS; IMINOSUGARS; 1-DEOXYNOJIRIMYCIN; AZASUGARS; SUGAR; GALACTOSIDASE; GLUCOSIDASE; NOJIRIMYCIN;

D O I：

10.1016/j.jfluchem.2011.05.031

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The straightforward synthesis of monofluorinated isofagomine analogues 1-3 was described. The synthetic strategy featured that the chiral carbon center bearing fluorine atom was constructed stereoselectively via silicon-induced Reformatskii-Claisen rearrangement of allyl bromofluoroacetate. These compounds were tested for inhibition of five glycosidases. The 3S,4R,5R isomer 3 has been found to be a potent inhibitor against beta-glucosidase from almonds with K-i value of 11.9 mu M. (C) 2011 Elsevier B.V. All rights reserved.

引用

页码：838 / 845

页数：8

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