Novel, lipophilic derivatives of 2,5-dideoxy-2,5-imino-D-mannitol (DMDP) are powerful β-glucosidase inhibitors

被引:38
作者
Wrodnigg, TM
Withers, SG
Stütz, AE
机构
[1] Graz Univ Technol, Glycogrp, Inst Organ Chem, A-8010 Graz, Austria
[2] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada
基金
奥地利科学基金会;
关键词
D O I
10.1016/S0960-894X(01)00126-3
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Novel derivatives of the D-glucosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol bearing lipophilic aliphatic or aromatic amides attached to C-l have been found to inhibit P-glucosidase from Agrobacterium sp. in the nanomolar range. One of them, a coumarin derivative. ranks amongst the most active compounds in the class of reversible glycosidase inhibitors of the iminoalditol type. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1063 / 1064
页数:2
相关论文
共 10 条
[1]  
[Anonymous], 1994, ANGEW CHEM, V106, P1858
[2]   ISOFAGOMINE, A POTENT, NEW GLYCOSIDASE INHIBITOR [J].
JESPERSEN, TM ;
DONG, WL ;
SIERKS, MR ;
SKRYDSTRUP, T ;
LUNDT, I ;
BOLS, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (17) :1778-1779
[3]  
Legler G, 1996, CARBOHYD RES, V292, P91
[4]  
Panday N, 2000, HELV CHIM ACTA, V83, P58, DOI 10.1002/(SICI)1522-2675(20000119)83:1<58::AID-HLCA58>3.3.CO
[5]  
2-B
[6]   Enzymatic synthesis of disaccharides using Agrobacterium sp. β-glucosidase [J].
Prade, H ;
MacKenzie, LF ;
Withers, SG .
CARBOHYDRATE RESEARCH, 1997, 305 (3-4) :371-381
[7]  
Stutz A.E., 1999, IMINOSUGARS GLYCOSID
[8]   2,5-DIHYDROXYMETHYL-3,4-DIHYDROXYPYRROLIDINE IN LEAVES OF DERRIS-ELLIPTICA [J].
WELTER, A ;
JADOT, J ;
DARDENNE, G ;
MARLIER, M ;
CASIMIR, J .
PHYTOCHEMISTRY, 1976, 15 (05) :747-749
[9]   Synthesis of 1-amino-1,2,5-trideoxy-2,5-imino-D-mannitol, a novel analogue of the powerful glucosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol, via an Amadori rearrangement of 5-azido-5-deoxy-D-glucofuranose [J].
Wrodnigg, TM ;
Stutz, AE ;
Withers, SG .
TETRAHEDRON LETTERS, 1997, 38 (31) :5463-5466
[10]   Biologically active 1-aminodeoxy and 1-O-alkyl derivatives of the powerful D-glucosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol [J].
Wrodnigg, TM ;
Gaderbauer, W ;
Greimel, P ;
Häusler, H ;
Sprenger, FK ;
Stütz, AE ;
Virgona, C ;
Withers, SG .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 2000, 19 (08) :975-990