Synthesis and biological evaluation of guanidine-type iminosugars

被引：30

作者：

Aguilar, Matilde ^{[1
]}

Diaz-Perez, Paula ^{[1
]}

Isabel Garcia-Moreno, M. ^{[1
]}

Ortiz Mellet, Carmen ^{[1
]}

Garcia Fernandez, Jose M. ^{[2
]}

机构：

[1] Univ Seville, Fac Quim, Dept Quim Organ, E-41012 Seville, Spain

[2] Univ Seville, CSIC, Inst Invest Quim, E-41092 Seville, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 05期

关键词：

D O I：

10.1021/jo702374f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The preparation of carbohydrate mimics in which the endocyclic oxygen has been replaced by a guanidine-type nitrogen atom is reported. The synthetic strategy involves the furanose -> piperidine rearrangement of 5-deoxy-5guanidino-L-idose precursors. The reaction proceeds through elimination of water to give 3-oxopiperidines, which were isolated as the corresponding hydrates. Biological evaluation of the new glycomimetics evidenced a strong influence of the nature of the substituents at the nitrogen atoms on the glycosidase inhibitory properties.

引用

页码：1995 / 1998

页数：4

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