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Article Dans Une Revue Tetrahedron Année : 2014

Synthesis and glycosidase inhibition properties of triazole-linked calixarene–iminosugar clusters

Résumé

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.

Domaines

Chimie
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Dates et versions

hal-03619349 , version 1 (25-03-2022)

Identifiants

Citer

Alberto Marra, Renaud Zelli, Giuseppe d'Orazio, Barbara La Ferla, Alessandro Dondoni. Synthesis and glycosidase inhibition properties of triazole-linked calixarene–iminosugar clusters. Tetrahedron, 2014, 70 (49), pp.9387-9393. ⟨10.1016/j.tet.2014.10.035⟩. ⟨hal-03619349⟩
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