The synthesis and biological evaluation of 1-C-alkyl-L-arabinoiminofuranoses, a novel class of α-glucosidase inhibitors

被引：35
作者：
Natori, Yoshihiro [1 ]
Imahori, Tatsushi [1 ]
Murakami, Keiichi [1 ]
Yoshimura, Yuichi [1 ]
Nakagawa, Shinpei [2 ]
Kato, Atsushi [2 ]
Adachi, Isao [2 ]
Takahata, Hiroki [1 ]
机构：
[1] Tohoku Pharmaceut Univ, Fac Pharmaceut Sci, Sendai, Miyagi 9818558, Japan
[2] Toyama Univ, Dept Hosp Pharm, Toyama 9300194, Japan
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2011年 / 21卷 / 02期
基金：
日本学术振兴会;
关键词：
1-C-Alkyl-L-arabinoiminofuranose; alpha-Glucosidase inhibitor; Asymmetric allylic alkylation; Negishi cross coupling; Type; 2; diabetes; GLYCOGEN-DEGRADING ENZYMES; CHIRAL BUILDING-BLOCK; ASYMMETRIC-SYNTHESIS; SUGAR MIMICS; ROUTE; STEREOISOMERS; GLYCOSIDASES; ENANTIOMERS; DERIVATIVES; CYCLIZATION;
D O I：
10.1016/j.bmcl.2010.11.112
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
The asymmetric synthesis of 1-C-alkyl-L-arabinoiminofuranoses 1 was achieved by asymmetric allylic alkylation (AAA), ring closing metathesis (RCM), and Negishi cross coupling as key reactions. Some of the prepared compounds showed potent inhibitory activities towards intestinal maltase, with IC50 values comparable to those of commercial drugs such as acarbose, voglibose, and miglitol, which are used in the treatment of type 2 diabetes. Among them, the inhibitory activity (IC50 = 0.032 mu M) towards intestinal sucrase of 1c was quite strong compared to the above commercial drugs. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：738 / 741
页数：4
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