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Fluorinated hydroxypiperidines as selective β-glucosidase inhibitors†
Clothilde Le Guen,Teresa Mena-Barragán,Carmen Ortiz Mellet,David Gueyrard,Emmanuel Pfund,Thierry Lequeux
Organic & Biomolecular Chemistry Pub Date : 04/28/2015 00:00:00 , DOI:10.1039/C5OB00721F
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
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