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
收藏
页码：3642 / 3649
页数：8
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