Synthesis of polyhydroxylated azetidine iminosugars and 3-hydroxy-N-methylazetidine-2-carboxylic acid from D-glucose

被引：10

作者：

Lawande, Pravin P. ^{[1
]}

Sontakke, Vyankat A. ^{[1
]}

Nair, Roopa J. ^{[2
]}

Khan, Ayesha ^{[3
]}

Sabharwal, Sushma G. ^{[2
]}

Shinde, Vaishali S. ^{[1
]}

机构：

[1] Savitribai Phule Pune Univ, Dept Chem, Garware Res Ctr, Pune 411007, Maharashtra, India

[2] Savitribai Phule Pune Univ, Dept Chem, Div Biochem, Pune 411007, Maharashtra, India

[3] Savitribai Phule Pune Univ, Dept Chem, Pune 411007, Maharashtra, India

来源：

TETRAHEDRON | 2015年 / 71卷 / 31期

关键词：

Azetidine; Iminosugars; Glycosidase inhibitory activity; Mitsunobu reaction; D-Glucose; STEREOSELECTIVE-SYNTHESIS; GLYCOSIDASE INHIBITORS; CYCLIZATION; POTENT; ANALOGS; SERIES; RING; PIPERIDINE; STRATEGIES; DISCOVERY;

D O I：

10.1016/j.tet.2015.05.057

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The azetidine iminosugars, (2S,3R)-2-((R)-1,2-dihydroxyethyl)azetidin-3-ol 3, (2R,3R)-2-(hydroxymethyl) azetidin-3-ol 4, and (25,3R)-3-hydroxy-N-methylazetidine-2-carboxylic acid 5 were synthesized from D-glucose derived 3-N-benzyloxycarbonyl-3-deoxy-1,2-O-isopropylidene-alpha-D-xylofuranose 8 using intramolecular Mitsunobu reaction as a key step. The glycosidase inhibitory activity of compounds 3-5 was screened against various enzymes. Amongst all synthesized compounds, the N-methylated compound 5 exhibited significant inhibitory activity against amyloglucosidase from Aspergillus niger in micro molar range. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：5085 / 5090

页数：6

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