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LIN Li, XU Qing, TANG Yan-Hui, CHEN Guo-Rong. Synthesis and Anti-tumor Activity of 6-O-Benzoyl C-Glycosyl Benzoquinone[J]. Chinese Journal of Applied Chemistry,
;2007, 24(10): 1109-1114.
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Galactopyranose and glucopyranose with 6-position hydroxyl were conveniently synthesized by selective protection and deprotection of isopropylidene group and benzyl group respectively. Selective benzoylation on 6-position of galactose and glucose could be achieved from the 6-position hydroxyl compounds and then β-aryl C-glycoside intermediates were obtained with high stereoselectivity by means of introducing the glycosyl donors onto 1,4-dimethoxyl benzene. Under moderate oxidation with CAN(ceric ammonium nitrate), 6-O-benzoyl C-glycosyl benzoquinones were prepared and for of them have not been reported. The structures of target compounds were confirmed by 1H NMR, 13C NMR and HRMS spectroscopy. Anti-tumor activity tests including IC50 by MTT tetrazolium dye assay against human melanoma A375 cell line were carried out. The results show that 6-O-benzoyl C-glycosyl benzoquinones possess moderate anti-tumor activity. This character will make them useful in the structure modification and discovery of some potential antitumor with high selectivity and high activity.
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