Halogenated D-xylono-δ-lactams: synthesis and enzyme inhibition study

Carbohydr Res. 2015 Jan 30:402:215-24. doi: 10.1016/j.carres.2014.10.023. Epub 2014 Oct 31.

Abstract

A concise synthesis of four C-3 fluoro/chloro-D-xylono-δ-lactams 3/4 has been reported. The methodology involves Corey-Link approach with suitably protected 3-oxo-D-gluco-furanose to introduce F/Cl as well as ester/amide functionalities at C-3 of glucose. In next steps, 5,6-O-isopropylidene group was converted to the 5-azido xylosugars that on opening of 1,2-acetonide group, and intramolecular Schmidt-Boyer reaction with TFA/H2O, in one pot, afforded lactams 3/4. Conformational aspect of δ-lactams was studied by the 1H NMR spectroscopy. The halogenated δ-lactams 3/4 showed no inhibition against different glycosidase enzymes.

Keywords: Conformations; Halogen; Iminosugars; Inhibitors; Lactams.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azides / chemistry
  • Carbohydrate Conformation
  • Catalysis
  • Chemistry Techniques, Synthetic
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Furans / chemistry
  • Glucose / chemistry
  • Glycoside Hydrolases / antagonists & inhibitors*
  • Halogenation*
  • Lactams / chemical synthesis*
  • Lactams / chemistry
  • Lactams / pharmacology*
  • Stereoisomerism

Substances

  • Azides
  • Enzyme Inhibitors
  • Furans
  • Lactams
  • Glycoside Hydrolases
  • Glucose