Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (03): 535-541.DOI: 10.6023/cjoc201210035 Previous Articles     Next Articles



娄定辉, 汪钢强, 夏立, 陈凌, 汪秋安   

  1. 湖南大学化学化工学院 长沙 410082
  • 收稿日期:2012-10-18 修回日期:2012-12-13 发布日期:2012-12-18
  • 通讯作者: 汪秋安
  • 基金资助:

    湖南省研究生科研创新(No. CX2012B160)和湖南省科技计划(No. 2011FJ3214)资助项目.

Synthesis and Biological Activity of Novel Flavonoids Galactoconjugates

Lou Dinghui, Wang Gangqiang, Xia Li, Chen Ling, Wang Qiuan   

  1. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082
  • Received:2012-10-18 Revised:2012-12-13 Published:2012-12-18
  • Supported by:

    Project supported by the Hunan Provincial Innovation Foundation for Postgraduate (No. CX2012B160) and the Science and Technology Planning Project of Hunan Province (No. 2011FJ3214).

Five flavonoids 5,7,3',4'-tetramethoxyflavonol (1), 5,7,3'-tribenzyloxy-4'-methoxy flavonol (2), 5,7,4'-trimethoxy- flavonol (3), acacetin (4) and 5,7-dihydroxy-4'-benzyloxyflavone (5) were synthesized from diosmetin or rhoifolin by O-methylation, dehydrogenation, glycoside hydrolysis, O-benzylation and dimethyldioxirane (DMDO) oxidation. Based on “Click chemistry”, ten novel flavonoids galactoconjugates 1120 were synthesized in good yield using copper-mediated 1,3-dipolar cycloaddition reactions of acetylgalactose azides and alkynyl-substituted flavonoids 610. Their biological activities against five human cancer cell lines were evaluated by the standard MTT method. The results showed that 11, 13 and 20 exhibited moderate cytotoxicity against HL-60, SMMC-7721, MCF-7, SW480 and A-549 cancer cell lines.

Key words: flavonoids, galactoconjugates, Click chemistry, synthesis, biological activity