Diversity-Oriented Synthesis and Biological Evaluation of Iminosugars from Unprotected 2-Deoxy-d-ribose

被引：10

作者：

Malinowski, Maciej ^{[1
]}

Rowicki, Tomasz ^{[1
]}

Guzik, Patrycja ^{[1
]}

Wielechowska, Monika ^{[1
]}

Sobiepanek, Anna ^{[1
]}

Sas, Wojciech ^{[1
]}

机构：

[1] Warsaw Univ Technol, Fac Chem, Ul Noakowskiego 3, PL-00664 Warsaw, Poland

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 21期

关键词：

Iminosugars; Nitrones; Carbohydrates; Cycloaddition; Biological activity; Nitrogen heterocycles; AQUEOUS-MEDIA; C-GLYCOSIDES; PHARMACOLOGICAL CHAPERONES; GALACTOSIDASE INHIBITORS; CHEMICAL-SYNTHESIS; CONVENIENT ROUTE; CHAIN ELONGATION; SUGARS; DERIVATIVES; METAL;

D O I：

10.1002/ejoc.201600459

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An exceptionally short synthesis of novel indolizidine-, quinolizidine-, and piperidine-based iminosugars from unprotected 2-deoxy-d-ribose by intramolecular 1,3-dipolar cycloaddition of sugar-derived N-(3-alkenyl)nitrones has been accomplished. The use of the 2-deoxy carbohydrate also enabled us to confirm the previously proposed mechanism for the alteration of the stereochemical course of the intramolecular 1,3-dipolar cycloaddition observed for an unprotected sugar-derived nitrone. Biological assays of the six new iminosugars revealed a slight inhibition activity of the indolizidine derivative 7a, whereas, interestingly, the two quinolizidine iminosugars 5a and 5b appeared to be weak glycosidase activators.

引用

页码：3642 / 3649

页数：8

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