Synthesis of Δ4-β-D-glucopyranosiduronic acids as mimetics of 2,3-unsaturated sialic acids for sialidase inhibition

被引:22
作者
Florio, P [1 ]
Thomson, RJ [1 ]
Alafaci, A [1 ]
Abo, S [1 ]
von Itzstein, M [1 ]
机构
[1] Monash Univ, Dept Med Chem, Parkville, Vic 3052, Australia
关键词
D O I
10.1016/S0960-894X(99)00331-5
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Mimetics of Neu5Ac2en and KDN2en, based on Delta(4)-beta-D-glucopyranosiduronic acids, have been synthesised. The Neu5Ac2en mimetic 5 showed inhibition of both bacterial and viral sialidases, with inhibition of the viral sialidase being comparable to that of Neu5Ac2en itself. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2065 / 2068
页数:4
相关论文
共 23 条
[1]   SYNTHESIS OF 6-CARBON, 7-CARBON AND 8-CARBON SUGAR ANALOGS OF POTENT ANTIINFLUENZA 2,3-DIDEHYDRO-2,3-DIDEOXY-N-ACETYLNEURAMINIC ACID-DERIVATIVES [J].
BAMFORD, MJ ;
PICHEL, JC ;
HUSMAN, W ;
PATEL, B ;
STORER, R ;
WEIR, NG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (09) :1181-1187
[2]   CRYSTAL-STRUCTURE OF VIBRIO-CHOLERAE NEURAMINIDASE REVEALS DUAL LECTIN-LIKE DOMAINS IN ADDITION TO THE CATALYTIC DOMAIN [J].
CRENNELL, S ;
GARMAN, E ;
LAVER, G ;
VIMR, E ;
TAYLOR, G .
STRUCTURE, 1994, 2 (06) :535-544
[3]  
HEYNS K, 1972, METHODS CARBOHYDR CH, V6, P342
[4]   INHIBITION OF SIALIDASES FROM VIRAL, BACTERIAL AND MAMMALIAN SOURCES BY ANALOGS OF 2-DEOXY-2,3-DIDEHYDRO-N-ACETYLNEURAMINIC ACID MODIFIED AT THE C-4 POSITION [J].
HOLZER, CT ;
VONITZSTEIN, M ;
JIN, B ;
PEGG, MS ;
STEWART, WP ;
WU, WY .
GLYCOCONJUGATE JOURNAL, 1993, 10 (01) :40-44
[5]   A SYNTHESIS OF N-ACETYLNEURAMINIC ACID AND [6-H-2]-N-ACETYLNEURAMINIC ACID FROM N-ACETYL-D-GLUCOSAMINE [J].
JULINA, R ;
MULLER, I ;
VASELLA, A ;
WYLER, R .
CARBOHYDRATE RESEARCH, 1987, 164 :415-432
[6]  
Kiefel MJ, 1999, PROGR MED CHEM, V36, P1, DOI 10.1016/S0079-6468(08)70044-4
[7]   Structure-activity relationship studies of novel carbocyclic influenza neuraminidase inhibitors [J].
Kim, CU ;
Lew, W ;
Williams, MA ;
Wu, HW ;
Zhang, LJ ;
Chen, XW ;
Escarpe, PA ;
Mendel, DB ;
Laver, WG ;
Stevens, RC .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (14) :2451-2460
[8]   Influenza neuraminidase inhibitors possessing a novel hydrophobic interaction in the enzyme active site: Design, synthesis, and structural analysis of carbocyclic sialic acid analogues with potent anti-influenza activity [J].
Kim, CU ;
Lew, W ;
Williams, MA ;
Liu, HT ;
Zhang, LJ ;
Swaminathan, S ;
Bischofberger, N ;
Chen, MS ;
Mendel, DB ;
Tai, CY ;
Laver, WG ;
Stevens, RC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (04) :681-690
[9]  
Müller B, 1998, ANGEW CHEM INT EDIT, V37, P2893, DOI 10.1002/(SICI)1521-3773(19981102)37:20<2893::AID-ANIE2893>3.0.CO
[10]  
2-W