1,2,3-Triazoles and related glycoconjugates as new glycosidase inhibitors

A series of saccharidyl-triazoles structurally related to acarbose were prepared and tested as inhibitors of glycosidases. They share in common a 1,4,5-trisubstituted 1,2,3-triazole heterocycle as a functional element able to interact with the active site of the target enzymes. First, it was establi...

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Bibliographic Details
Published in:Tetrahedron 2005-09, Vol.61 (38), p.9118-9128
Main Authors: Périon, Régis, Ferrières, Vincent, Isabel García-Moreno, M., Ortiz Mellet, Carmen, Duval, Raphaël, García Fernández, José M., Plusquellec, Daniel
Format: Article
Language:English
Subjects:
Carbohydrates
Glycosidase inhibition
Glycosylation
Triazoles
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Summary:A series of saccharidyl-triazoles structurally related to acarbose were prepared and tested as inhibitors of glycosidases. They share in common a 1,4,5-trisubstituted 1,2,3-triazole heterocycle as a functional element able to interact with the active site of the target enzymes. First, it was established that the heterocyclic core exhibits a moderate but highly selective α-glucosidase inhibitory activity. Then, it was confirmed that the inhibitory properties could be modulated by conjugation from one to five carbohydrate residues. The present study includes the regio- and stereocontrolled synthesis of novel non-fused 1,2,3-triazolo-pseudooligosaccharides as well as their evaluation as new glycosidase inhibitors. The synthesis of new glycosylated triazoles and their inhibiting effects for a panel of glycosidases are reported.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.07.033