Synthesis of substituted exo-glucals via a modified Julia olefination and identification as selective β-glucosidase inhibitors

Org Biomol Chem. 2014 Jan 28;12(4):690-9. doi: 10.1039/c3ob41926f.

Abstract

A series of fluorine and non-fluorine-substituted C-glucosylidenes (exo-glucals) has been synthesized via a modified Julia olefination. The deprotected exo-glucals were prepared in five steps from commercially available d-gluconolactone. The evaluation of this original family of compounds against a panel of glycosidases showed a highly specific in vitro activity towards mammalian β-glucosidase depending on the double bond substituents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Glycosides
  • Molecular Structure
  • Monosaccharides / chemical synthesis
  • Monosaccharides / chemistry
  • Monosaccharides / pharmacology*
  • Saccharomyces cerevisiae / enzymology
  • Structure-Activity Relationship
  • beta-Glucosidase / antagonists & inhibitors*
  • beta-Glucosidase / metabolism

Substances

  • Alkenes
  • C-glycoside
  • Enzyme Inhibitors
  • Glycosides
  • Monosaccharides
  • beta-Glucosidase