Synthesis and mannosidase inhibitory activity of 3-benzyloxymethyl analogs of swainsonine

被引:79
作者
Pearson, WH [1 ]
Guo, LY
机构
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
[2] Univ Michigan, Sch Pharm, Dept Med Chem, Ann Arbor, MI 48109 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(01)01777-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Swainsonine (3), an inhibitor of Golgi alpha -mannosidase II, is a clinical candidate for cancer treatment. In order to avoid potential problems arising from its co-inhibition of lysosomal mannosidases, we have synthesized 3-benzyloxymethyl analogs of swainsonine (17 and 18). Initial screening of these new compounds is reported. (C) 2001 Published by Elsevier Science Ltd.
引用
收藏
页码:8267 / 8271
页数:5
相关论文
共 47 条
[1]   THE SUBSTRATE-SPECIFICITY OF HUMAN LYSOSOMAL ALPHA-D-MANNOSIDASE IN RELATION TO GENETIC ALPHA-MANNOSIDOSIS [J].
ALDAHER, S ;
DEGASPERI, R ;
DANIEL, P ;
HALL, N ;
WARREN, CD ;
WINCHESTER, B .
BIOCHEMICAL JOURNAL, 1991, 277 :743-751
[2]   Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application [J].
Asano, N ;
Nash, RJ ;
Molyneux, RJ ;
Fleet, GWJ .
TETRAHEDRON-ASYMMETRY, 2000, 11 (08) :1645-1680
[3]  
DEGASPERI R, 1992, J BIOL CHEM, V267, P9706
[4]   Glycoprotein glycosylation and cancer progression [J].
Dennis, JW ;
Granovsky, M ;
Warren, CE .
BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS, 1999, 1473 (01) :21-34
[5]   CARBONOYLOXY ANALOGS OF THE ANTIMETASTATIC DRUG SWAINSONINE - ACTIVATION IN TUMOR-CELLS BY ESTERASES [J].
DENNIS, JW ;
WHITE, SL ;
FREER, AM ;
DIME, D .
BIOCHEMICAL PHARMACOLOGY, 1993, 46 (08) :1459-1466
[6]  
Dennis JW, 1999, BIOESSAYS, V21, P412, DOI 10.1002/(SICI)1521-1878(199905)21:5<412::AID-BIES8>3.0.CO
[7]  
2-5
[8]  
DIBELLO IC, 1989, BIOCHEM J, V259, P855
[9]   THE STORAGE PRODUCTS IN GENETIC AND SWAINSONINE-INDUCED HUMAN MANNOSIDOSIS [J].
DIBELLO, IC ;
DORLING, P ;
WINCHESTER, B .
BIOCHEMICAL JOURNAL, 1983, 215 (03) :693-696
[10]  
Dorling P., 1983, Biochemical Society Transactions, V11, P717