Sugar hydrazide imides: a new family of glycosidase inhibitors

被引：6
|
作者：
Lindback, Emil [1 ]
Lopez, Oscar [2 ]
Tobiesen, Adne [1 ]
Fernandez-Bolanos, Jose G. [2 ]
Sydnes, Magne O. [1 ]
机构：
[1] Univ Stavanger, Dept Math & Nat Sci, Fac Sci & Technol, NO-4036 Stavanger, Norway
[2] Univ Seville, Dept Organ Chem, Prof Garcia Gonzalez 1, E-41012 Seville, Spain
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 41期
关键词：
TRANSITION-STATE; ALPHA-GLUCOSIDASE; BETA-GLUCOSIDASE; 1-DEOXYNOJIRIMYCIN DERIVATIVES; N-BUTYLDEOXYNOJIRIMYCIN; AMIDINE; IMINOSUGARS; POTENT; ANALOG; GLUCOSYLCERAMIDASE;
D O I：
10.1039/c7ob01673e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The preparation of a novel type of iminosugar including a hydrazide imide moiety is described. The sugar hydrazide imides (3S, 4S, 5R, 6R)-1-amino-3,4,5-trihydroxy-6-(hydroxymethyl)-2-iminopiperidine acetate and (3S, 4S, 5R, 6R)-3,4,5-trihydroxy-6-(hydroxymethyl)- 2-imino-1-(methylamino) piperidine acetate presented here behave as inhibitors of alpha/beta-glucosidases in the low micromolar concentration range. The former inhibitor displays a pH-dependent inhibition of beta-glucosidase. The N-methylated counterpart behaves as an anomer-selective competitive micromolar inhibitor of alpha-glucosidase.
引用
收藏
页码：8709 / 8712
页数：4
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