NATURAL PRODUCT RESEARCH AND DEVELOPMENT ›› 2019, Vol. 31 ›› Issue (7): 1258-1264. doi: 10.16333/j.1001-6880.2019.7.020

Special Issue: No.8

• Article • Previous Articles     Next Articles

Structural modification and antitumor activity of baicalein

CHEN Dang-hui,DENG Yan-ru,MOU Jia-jia*,JIA Yan   

  1. School of Chinese Materia Medica,Tianjin University of Traditional Chinese Medicine,Tianjin 301617,China
  • Online:2019-07-29 Published:2019-07-29

Abstract: In order to improve the anti-tumor activity of baicalein,it was structurally modified.First,an amine methylene group is introduced to the 8-position by a mannich reaction,and then a different hydrophobic group is introduced to the 7-position (6-position) phenolic hydroxyl group by an acylation reaction.The target compound was evaluated for activity against MCF-7 tumor cells by the CCK-8 method.As a result,six target compounds were synthesized,and compound 2-6 are new compounds.Their structures were determined by a combination of 1H NMR,13C NMR,MS and chemical methods.The chemical methods utilized the characteristics of the o-diphenol hydroxyl group of flavonoid,which could react with ruthenium chloride to confirm that the ester bond of the compounds was at the 7-position hydroxyl group.Activity experiments showed that the activity of the compound with an amine-methylene group that containing a nitrogen atom at the 8-position is stronger than the lead compound.And after the ester bond is introduced at the 7-position,the activity of most compounds becomes better.

Key words: baicalein, structural modification, mannich reaction, acylation reaction, structure confirmation, antitumor

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