Castanospermine-trehazolin hybrids:: a new family of glycomimetics with tuneable glycosidase inhibitory properties

被引：35

作者：

García-Moreno, MI

Díaz-Pérez, P

Mellet, CO

Fernández, JMG

机构：

[1] Univ Seville, Fac Quim, Dept Quim Organ, E-41071 Seville, Spain

[2] CSIC, Inst Invest Quim, E-41092 Seville, Spain

来源：

CHEMICAL COMMUNICATIONS | 2002年 / 08期

关键词：

D O I：

10.1039/b200162d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Bicyclic azasugar glycomimetics related to castanospermine and trehazolin have been prepared from sugar carbodiimides via aminooxazoline intermediates; preliminary enzyme inhibition tests showed a marked dependence of the selectivity and potency towards alpha and beta-glucosidases upon the nature of the exocyclic substituent.

引用

收藏

页码：848 / 849

页数：2

相关论文

共 17 条

[1] 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

[2] Synthesis and biological activity of natural aminocyclopentitol glycosidase inhibitors: Mannostatins, trehazolin, allosamidins, and their analogues [J].

Berecibar, A ;

Grandjean, C ;

Siriwardena, A .

CHEMICAL REVIEWS, 1999, 99 (03) :779-844

[3]

Blanco JLJ, 1997, CHEM COMMUN, P1969

[4] SIMPLE SYNTHESIS OF 1,5-DIDEOXY-1,5-IMINO-D-GLUCITOL(1-DEOXYNOJIRIMYCIN) AND 1,6-DIDEOXY-1,6-IMINO-D-GLUCITOL FROM D-GLUCOFURANURONO-6,3-LACTONE [J].

DAX, K ;

GAIGG, B ;

GRASSBERGER, V ;

KOLBLINGER, B ;

STUTZ, AE .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1990, 9 (04) :479-499

[5]

de Gracia IS, 1999, ORG LETT, V1, P1705

[6]

den Broek L.A.G.M., 1997, CARBOHYDRATES DRUG D, P471

[7]

Fernández JMG, 2000, ADV CARBOHYD CHEM BI, V55, P35

[8] Synthesis and evaluation of calystegine B2 analogues as glycosidase inhibitors [J].

García-Moreno, MI ;

Benito, JM ;

Mellet, CO ;

Fernández, JMG .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) :7604-7614

[9] Polyhydroxylated N-(thio)carbamoyl piperidines:: nojirimycin-type glycomimetics with controlled anomeric configuration [J].

García-Moreno, MI ;

Mellet, CO ;

Fernández, JMG .

TETRAHEDRON-ASYMMETRY, 1999, 10 (22) :4271-4275

[10] Chemistry and biology of trehazolins [J].

Kobayashi, Y .

CARBOHYDRATE RESEARCH, 1999, 315 (1-2) :3-15