Synthesis of beta-C-glycopyranosyl-1,4-naphthoquinone derivatives and their cytotoxic activity.
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.
Lin
Li
L
Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237, PR China.
He
Xiao-Peng
XP
Xu
Qing
Q
Chen
Guo-Rong
GR
Xie
Juan
J
D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D006801:Humans; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D013329:Structure-Activity Relationship
D006027:Glycosides; D009285:Naphthoquinones