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

Li Lin; Xiao-Peng He; Qing Xu; Guo-Rong Chen; Juan Xie

doi:10.1016/j.carres.2007.12.017

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.

Authors

Li Lin¹, Xiao-Peng He, Qing Xu, Guo-Rong Chen, Juan Xie

Affiliation

¹ Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237, PR China.

PMID: 18190900
DOI: 10.1016/j.carres.2007.12.017

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