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Issue 5, 2019
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Design, synthesis and glycosidase inhibition studies of novel triazole fused iminocyclitol-δ-lactams

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Abstract

Synthesis of novel triazole fused iminocyclitol-δ-lactams is described. The synthetic sequence involves the intermolecular [3 + 2] cycloaddition reaction of five-membered iminocyclitol derived azides with diethylacetylene dicarboxylate followed by intramolecular lactamisation, decarboxylation/reduction and final deprotection. Compound 3 is found to be a selective inhibitor of α-glucosidase from baker's yeast while two other compounds (2 and 4) that possess an additional hydroxymethyl group in the triazole ring are selective against β-galactosidase from E. coli. Docking studies suggest the significance of the lactam carbonyl group for effective binding of these inhibitors with the active sites through hydrogen bonding.

Graphical abstract: Design, synthesis and glycosidase inhibition studies of novel triazole fused iminocyclitol-δ-lactams

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Supplementary files

Article information


Submitted
12 Dec 2018
Accepted
02 Jan 2019
First published
03 Jan 2019

Org. Biomol. Chem., 2019,17, 1130-1140
Article type
Paper

Design, synthesis and glycosidase inhibition studies of novel triazole fused iminocyclitol-δ-lactams

V. Santhanam, P. Pant, B. Jayaram and N. G. Ramesh, Org. Biomol. Chem., 2019, 17, 1130
DOI: 10.1039/C8OB03084G

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