SYNTHESIS AND BIOLOGICAL-ACTIVITY OF C-6 MODIFIED DERIVATIVES OF THE GLUCOSIDASE INHIBITOR 1-DEOXYNOJIRIMYCIN

被引:19
作者
BERGER, A
DAX, K
GRADNIG, G
GRASSBERGER, V
STUTZ, AE
UNGERANK, M
LEGLER, G
BAUSE, E
机构
[1] GRAZ TECH UNIV,INST ORGAN CHEM,STREMAYRGASSE 16,A-8010 GRAZ,AUSTRIA
[2] UNIV COLOGNE,INST BIOCHEM,W-5000 COLOGNE,GERMANY
[3] UNIV BONN,INST PHYSIOL CHEM,W-5300 BONN,GERMANY
关键词
D O I
10.1016/S0960-894X(00)80648-4
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A novel 1-deoxynojirimycin derivative, (6S)-6-C-ethyl-1-deoxynojirimycin, was synthesized and tested on a set of alpha- and beta-glucosidases. Its enzyme inhibitory activity against alpha-glucosidases from yeast and rice was superior to those of 1,6-dideoxy-6-fluoronojirimycin, 1-deoxynojirimycin and its bicyclic analogue, castanospermine.
引用
收藏
页码:27 / 32
页数:6
相关论文
共 33 条
[1]   TOTAL SYNTHESES OF GALACTOSIDASE INHIBITORS (+)-GALACTOSTATIN AND (+)-1-DEOXYGALACTOSTATIN [J].
AOYAGI, S ;
FUJIMAKI, S ;
YAMAZAKI, N ;
KIBAYASHI, C .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :815-819
[2]   A NEW FAMILY OF 5-CARBON IMINOALDITOLS WHICH ARE POTENT GLYCOSIDASE INHIBITORS [J].
BERNOTAS, RC ;
PAPANDREOU, G ;
URBACH, J ;
GANEM, B .
TETRAHEDRON LETTERS, 1990, 31 (24) :3393-3396
[3]   SYNTHESIS OF (+)-1,5-DIDEOXY-1,5-IMINO-D-GALACTITOL, A POTENT ALPHA-D-GALACTOSIDASE INHIBITOR [J].
BERNOTAS, RC ;
PEZZONE, MA ;
GANEM, B .
CARBOHYDRATE RESEARCH, 1987, 167 :305-311
[4]  
BOSHAGEN B, 1989, 6TH EUR CARB M PRAG
[5]   THE CHEMISTRY OF THE 1-DEOXYNOJIRIMYCIN SYSTEM - SYNTHESIS OF 2-ACETAMIDO-1,2-DIDEOXYNOJIRIMYCIN FROM 1-DEOXYNOJIRIMYCIN [J].
BOSHAGEN, H ;
HEIKER, FR ;
SCHULLER, AM .
CARBOHYDRATE RESEARCH, 1987, 164 :141-148
[6]   SIMPLE SYNTHESIS OF 1,5,6-TRIDEOXY-6-FLUORO-1,5-IMINO-D-GLUCITE, THE FIRST FLUORINE-CONTAINING DERIVATIVE OF THE GLUCOSIDASE INHIBITOR 1-DEOXYNOJIRIMYCIN [J].
DAX, K ;
GRASSBERGER, V ;
STUTZ, AE .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1990, 9 (06) :903-908
[7]  
DAX K, 1991, IN PRESS CARBOHYDR R
[8]   MORANOLINE (1-DEOXYNOJIRIMYCIN) FERMENTATION AND ITS IMPROVEMENT [J].
EZURE, Y ;
MARUO, S ;
MIYAZAKI, K ;
KAWAMATA, M .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1985, 49 (04) :1119-1125
[9]   ISOLATION AND STRUCTURE OF AN UNUSUAL CYCLIC AMINO ALDITOL FROM A LEGUME [J].
FELLOWS, LE ;
BELL, EA ;
LYNN, DG ;
PILKIEWICZ, F ;
MIURA, I ;
NAKANISHI, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (22) :977-978
[10]  
FLEET GWJ, 1986, CHEM LETT, V7, P1051