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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 03: 535 - 541

DOI: https://doi.org/10.6023/cjoc201210035

Articles

Synthesis and Biological Activity of Novel Flavonoids Galactoconjugates

  • Lou Dinghui ,
  • Wang Gangqiang ,
  • Xia Li ,
  • Chen Ling ,
  • Wang Qiuan
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  • College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082

Received date: 2012-10-18

  Revised date: 2012-12-13

  Online 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).

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Abstract

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 11～20 were synthesized in good yield using copper-mediated 1,3-dipolar cycloaddition reactions of acetylgalactose azides and alkynyl-substituted flavonoids 6～10. 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

Cite this article

Lou Dinghui , Wang Gangqiang , Xia Li , Chen Ling , Wang Qiuan . Synthesis and Biological Activity of Novel Flavonoids Galactoconjugates[J]. Chinese Journal of Organic Chemistry, 2013 , 33(03) : 535 -541 . DOI: 10.6023/cjoc201210035

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