Synthesis of beta-C-glycopyranosyl-1,4-naphthoquinone derivatives and their cytotoxic activity

Carbohydr Res. 2008 Mar 17;343(4):773-9. doi: 10.1016/j.carres.2007.12.017. Epub 2007 Dec 25.

Abstract

Beta-C-Glucosyl and beta-C-galactosyl-1,4-dimethoxynaphthalenes have been synthesized using a F3CCO2Ag/SnCl4 promoted Friedel-Crafts electrophilic substitution reaction. Both glycosyl acetates and methyl glycosides can be used as glycosyl donors. Further oxidation afforded the corresponding beta-C-glycosyl-1,4-naphthoquinones. The in vitro cytotoxic activity of these compounds was evaluated against the A375 cell line.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Glycosides / toxicity*
  • Humans
  • Molecular Structure
  • Naphthoquinones / chemical synthesis*
  • Naphthoquinones / chemistry
  • Naphthoquinones / toxicity*
  • Structure-Activity Relationship

Substances

  • Glycosides
  • Naphthoquinones