Synthesis and evaluation as glycosidase inhibitors of 2,5-imino-D-glucitol and 1,5-imino-D-mannitol related derivatives

被引：36

作者：

McCort, I ^{[1
]}

Fort, S ^{[1
]}

Duréault, A ^{[1
]}

Depezay, JC ^{[1
]}

机构：

[1] Univ Paris 05, Chim & Biochim Pharmacol & Toxicol Lab, CNRS, F-75270 Paris 06, France

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2000年 / 8卷 / 01期

关键词：

C-2 symmetric bis-aziridine; azasugars; beta-D-glucosidase inhibitor; alpha-L-fucosidase inhibitor;

D O I：

10.1016/S0968-0896(99)00267-9

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：

Selectively functionalized 2,5-imino-D-glucitol and 1,5-imino-D-mannitol derivatives were synthesized and tested as precursors of hydrolytically resistant pseudo-disaccharides. Among them N-acetyl-6-amino-6-deoxy-2,5-imino-D-glucitol (11) and N-acetyl-6-amino-6-deoxy- 1,5-imino-D-mannitol (12) were found potent and specific inhibitors against beta-D-glucosidase and alpha-L-fucosidase, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：135 / 143

页数：9

共 19 条

[1] Aza-C-disaccharides: Synthesis of 6-deoxygalactonojirimycin beta-C(1->3) linked with D-altrofuranosides and D-galactose [J].

Baudat, A ;

Vogel, P .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (18) :6252-6260

[2] One step synthesis of sulfur and nitrogen linked aza-disaccharide precursors from D-mannitol derived bis-aziridines [J].

Campanini, L ;

Dureault, A ;

Depezay, JC .

TETRAHEDRON LETTERS, 1996, 37 (29) :5095-5098

[3] CONCISE SYNTHESIS OF NEW HOMOAZASUGARS - FULLY SUBSTITUTED, FUNCTIONALLY DIVERSE PYRROLIDINES [J].

CAMPANINI, L ;

DUREAULT, A ;

DEPEZAY, JC .

TETRAHEDRON LETTERS, 1995, 36 (44) :8015-8018

[4]

deRaadt A, 1997, TOP CURR CHEM, V187, P157

[5] Evaluation of isofagomine and its derivatives as potent glycosidase inhibitors [J].

Dong, WL ;

Jespersen, T ;

Bols, M ;

Skrydstrup, T ;

Sierks, MR .

BIOCHEMISTRY, 1996, 35 (08) :2788-2795

[6] 2,5-DISUBSTITUTED PYRROLIDINES FROM D-MANNITOL-DERIVED BIS-AZIRIDINES [J].

FITREMANN, J ;

DUREAULT, A ;

DEPEZAY, JC .

TETRAHEDRON LETTERS, 1994, 35 (08) :1201-1204

[7] Synthesis and biological evaluation of aza-C-disaccharides: (1->6), (1->4), and (1->1) linked sugar mimics [J].

Johns, BA ;

Pan, YT ;

Elbein, AD ;

Johnson, CR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (21) :4856-4865

[8] Intramolecular cyclization of C-2 symmetric and meso-iodo amino alcohols: A synthetic approach to azasugars [J].

Kang, SH ;

Ryu, DH .

TETRAHEDRON LETTERS, 1997, 38 (04) :607-610

[9]

LEGLER G, 1991, BIOCHIM BIOPHYS ACTA, P89

[10] USE OF DIHYDROXYACETONE PHOSPHATE DEPENDENT ALDOLASES IN THE SYNTHESIS OF DEOXYAZASUGARS [J].

LIU, KKC ;

KAJIMOTO, T ;

CHEN, LR ;

ZHONG, ZY ;

ICHIKAWA, Y ;

WONG, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (22) :6280-6289

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