A convenient synthesis of N-linked diglycose derivatives based on one-pot tandem Staudinger/aza-Wittig/reduction and biological evaluation

Carbohydr Res. 2013 May 3:372:15-22. doi: 10.1016/j.carres.2013.02.002. Epub 2013 Feb 24.

Abstract

A series of novel N-linked diglycose derivatives 9 and 10 were conveniently and directly synthesized based on the key step of one-pot tandem Staudinger/aza-Wittig/reduction reaction from the azido sugar and sugar-derived aldehyde followed by deprotection. The biological activities against glycosidases (α-amylase, α-glucosidase, and β-glucosidase) and HIV-RT and antitumor activity of these compounds were preliminarily evaluated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Amines / chemistry
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacology
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Carbohydrate Conformation
  • Chemistry Techniques, Synthetic
  • Disaccharidases / chemical synthesis*
  • Disaccharidases / pharmacology*
  • Drug Evaluation, Preclinical / methods
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Glycoside Hydrolase Inhibitors
  • HIV Reverse Transcriptase / antagonists & inhibitors
  • HeLa Cells / drug effects
  • Humans
  • alpha-Amylases / antagonists & inhibitors

Substances

  • Aldehydes
  • Amines
  • Anti-HIV Agents
  • Antineoplastic Agents
  • Enzyme Inhibitors
  • Glycoside Hydrolase Inhibitors
  • HIV Reverse Transcriptase
  • Disaccharidases
  • alpha-Amylases