Synthesis of bivalent lactosides based on terephthalamide, N,N′-diglucosylterephthalamide, and glycophane scaffolds and assessment of their inhibitory capacity on medically relevant lectins

Journal of Organic Chemistry

Volumn 74, Issue 23, 2009, Pages 9010-9026

  Leyden, Rosaria ^a   Velasco Torrijos, Trinidad ^a   André, Sabine ^b   Gouin, Sebastien ^a   Gabius, Hans Joachim ^b   Murphy, Paul V ^a,c  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

^b UNIVERSITY OF MUNICH   (Germany)

^c NATIONAL UNIVERSITY OF IRELAND   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

A PLANTS; AZIDE-ALKYNE CYCLOADDITION; CELL ASSAYS; CHEMICAL EQUATIONS; CONJUGATION CHEMISTRY; DEGREE OF FLEXIBILITY; GALECTINS; GLUCURONIC ACIDS; GLYCANS; GLYCOSIDATIONS; GLYCOSYL; HUMAN CELLS; LACTOSE RESIDUE; PLANT TOXINS; POTENT INHIBITOR; RING CLOSING METATHESIS; SOLID-PHASE; TEREPHTHALAMIDES; TOXIN BINDING; UGI REACTION;

ACETYLENE; AMIDES; AMINES; ANTIGEN-ANTIBODY REACTIONS; ASSAYS; COMPLEXATION; GLUCOSE; GLYCOPROTEINS; PLANT SHUTDOWNS; SYNTHESIS (CHEMICAL); TOXIC MATERIALS;

SCAFFOLDS;

1 4 DI[BETA DEXTRO GALACTOPYRANOSYL(1-4) BETA DEXTRO GLUCOPYRANOSYL(1-3) 1 O PROPYL ALPHA DEXTRO GLUCOPYRANURONAMIDO]BENZENE; 1,4 DI[1 [BETA DEXTRO GALACTOPYRANOSYL(1-4) BETA DEXTRO GLUCOPYRANOSYL] 1,2,3 TRIAZOL 4 YLMETHYLOXY]BENZENE; 1,4 DI[[BETA DEXTRO GALACTOPYRANOSYL(1-4) BETA DEXTRO GLUCOPYRANOSYL](1-3) 1 AZIDO 1 DEOXY BETA DEXTRO GLUCOPYRANURONAMIDOMETHYL]BENZENE; AMIDE; AMINE; AZIDE; COPPER; DIAMINE DERIVATIVE; GALECTIN; GALECTIN 3; GLUCURONIC ACID; GLYCAN; GLYCOPHANE; GLYCOPROTEIN; LACTOSE; LACTOSIDE; LECTIN; N,N' DI(BETA DEXTRO GALACTOPYRANOSYL(1-4) BETA DEXTRO GLUCOPYRANOSYL(1-3) BETA DEXTRO GLUCOPYRANOSYL]TEREPHTHALAMIDE; N,N' DI[BETA D GALACTOPYRANOSYL BETA (1-4) BETA DEXTRO GLUCOPYRANOSE] N,N' DI[(1 METHOXYCARBONYL)METHYLAMINO 2 OXOETHYL]TEREPHTHALAMIDE; N,N' DI[BETA DEXTRO GALACTOPYRANOSYL(1-4) BETA DEXTRO GLUCOPYRANOSYL(1-4) BETA DEXTRO GLUCOPYRANOSYL]TEREPHTALAMIDE; N,N' DI[BETA DEXTRO GALACTOPYRANOSYL(1-4) O BETA DEXTRO GLUCOPYRANOSYL(1-6) BETA DEXTRO GLUCOPYRANOSYL]TEREPHTALAMIDE; P XYLYLENEDIAMINE; PLANT TOXIN; PROTEIN INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BIOLOGICAL ACTIVITY; CATALYSIS; CELL; CELL ASSAY; CELL PROTECTION; CONJUGATION; CONTROLLED STUDY; CROSS COUPLING REACTION; CYCLOADDITION; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; GLYCOSIDATION; HEMAGGLUTINATION; HUMAN; HUMAN CELL; NONHUMAN; PROTEIN BINDING; PROTEIN DEGRADATION; RING CLOSING METATHESIS; SENSOR; SOLID; STRUCTURE ACTIVITY RELATION;

AGGLUTINATION TESTS; CELL ADHESION; DRUG DESIGN; ERYTHROCYTES; GALECTINS; GLYCOPROTEINS; GLYCOSIDES; HUMANS; IMMOBILIZED PROTEINS; LECTINS; PHTHALIMIDES; PLANT LECTINS;

EID: 72249089323     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901667r     Document Type: Article

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