Synthesis and biological activities of novel isoxazoline-linked pseudodisaccharide derivatives

Carbohydr Res. 2012 Apr 1:351:7-16. doi: 10.1016/j.carres.2011.11.025. Epub 2011 Dec 4.

Abstract

A series of novel isoxazoline linked pseudodisaccharide derivatives were regiospecifically synthesized by 1,3-dipolar cycloaddition of α-allyl-C-glycopyranosides and sugar-derived nitrile oxides with good yields. The structures of the compounds were characterized by NMR spectroscopy and MS spectrometry and confirmed by the X-ray crystallographic analysis of compound ((5S)-3-(2,3-O-isopropylidene-5-deoxy-d-lyxofuranose-4-yl)isoxazoline-5-yl) methyl α- C-D-galactopyranoside. Their biological activities against glycosidases (α-amylase, α-glucosidase, and β-glucosidase) and HIV-RT, and antitumor activity were preliminarily evaluated. Some of them exhibited potent inhibitory activity to HIV-RT.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Disaccharides / chemical synthesis
  • Disaccharides / chemistry*
  • Disaccharides / pharmacology*
  • Glycoside Hydrolases / antagonists & inhibitors
  • HIV Reverse Transcriptase / antagonists & inhibitors
  • Humans
  • Isoxazoles / chemistry*
  • Reverse Transcriptase Inhibitors / chemical synthesis
  • Reverse Transcriptase Inhibitors / chemistry*
  • Reverse Transcriptase Inhibitors / pharmacology*

Substances

  • Antineoplastic Agents
  • Disaccharides
  • Isoxazoles
  • Reverse Transcriptase Inhibitors
  • HIV Reverse Transcriptase
  • Glycoside Hydrolases