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Synthesis and glycosidase inhibition properties of triazole-linked calixarene–iminosugar clusters
- Publication Year :
- 2014
-
Abstract
- Calixarene–iminosugar derivatives bearing four 1-deoxynojirimycin units at the upper or lower rim of calix[4]arenes in a fixed cone conformation were synthesized by copper-catalyzed azide-alkyne cycloaddition (CuAAC) and their inhibitory activity was evaluated against five glycosidases. Modest but significant affinity enhancements of up to seven per 1-deoxynojirimycin unit over the monovalent iminosugar derivative were observed for the inhibition of Jack bean ( Canavalia ensiformis ) α-mannosidase. It was also demonstrated that the residual copper ions did not contribute to the inhibitory properties of the newly prepared calixarene-based multivalent iminosugars.
- Subjects :
- 1-Deoxynojirimycin derivatives
biology
Stereochemistry
Calix[4]arenes, Clusters, 1-Deoxynojirimycin derivatives, Glycosidases inhibitors, Iminosugars
Organic Chemistry
Iminosugar
Triazole
Calix[4]arenes
chemistry.chemical_element
Clusters
Glycosidases inhibitors
Iminosugars
biology.organism_classification
Biochemistry
Copper
Cycloaddition
chemistry.chemical_compound
Cone conformation
chemistry
Canavalia ensiformis
Drug Discovery
Calixarene
CHIM/06 - CHIMICA ORGANICA
Glycoside hydrolase
Subjects
Details
- Language :
- English
- Database :
- OpenAIRE
- Accession number :
- edsair.doi.dedup.....370c19c8db9dfda8f673724ca04fafa0