Issue 21, 2015

Fluorinated hydroxypiperidines as selective β-glucosidase inhibitors

Abstract

A new series of fluoroallylamines derived from hydroxypiperidines was prepared and evaluated against various glycosidases. The short synthesis of target molecules involved the modified Julia reaction between aldehydes and functionalized fluoroaminosulfones. Biological studies revealed good and selective β-glucosidase inhibition in the micromolar range for two compounds, while the non-fluorinated analogue of the most active compound was selective towards α-glucosidase.

Graphical abstract: Fluorinated hydroxypiperidines as selective β-glucosidase inhibitors

Supplementary files

Article information

Article type
Paper
Submitted
10 Apr 2015
Accepted
28 Apr 2015
First published
28 Apr 2015

Org. Biomol. Chem., 2015,13, 5983-5996

Author version available

Fluorinated hydroxypiperidines as selective β-glucosidase inhibitors

C. Le Guen, T. Mena-Barragán, C. Ortiz Mellet, D. Gueyrard, E. Pfund and T. Lequeux, Org. Biomol. Chem., 2015, 13, 5983 DOI: 10.1039/C5OB00721F

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