Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the α-glucosidase inhibitory activity

被引：58

作者：

Muraoka, O ^{[1
]}

Yoshikai, K

Takahashi, H

Minematsu, T

Lu, GX

Tanabe, G

Wang, T

Matsuda, H

Yoshikawa, M

机构：

[1] Kinki Univ, Sch Pharmaceut Sci, 3-4-1 Kowakae, Higashiosaka, Osaka 5778502, Japan

[2] Kyoto Pharmaceut Univ, Yamashina Ku, Kyoto 6078412, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2006年 / 14卷 / 02期

基金：

日本学术振兴会;

关键词：

alpha-glucosidase inhibitor; salacinol; deoxygenated salacinol; thiosugar;

D O I：

10.1016/j.bmc.2005.08.040

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Three analogs (5, 6, and 7) lacking polar substituents in the side chain of a naturally occurring a-glucosidase inhibitor, salacinol (la), were synthesized by the coupling reaction of a thiosugar, 1,4-dideoxy-1,4-epithio-D-arabinitol (3), with cyclic sulfates (8, 9, and 10), and their a-glucosidase inhibitory activities were examined. All these simpler analogs (5, 6, and 7) showed less inhibitory activity compared to la, and proved the importance of cooperative role of the polar substituents for the a-glucosidase inhibitory activity. A practical synthetic route to 3 starting from D-xylose is also described. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：500 / 509

页数：10

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