NATURAL PRODUCT RESEARCH AND DEVELOPMENT ›› 2018, Vol. 30 ›› Issue (10): 1714-1720. doi: 10.16333/j.1001-6880.2018.10.09

• Article • Previous Articles     Next Articles

Design,Synthesis and Structure-Activity Relationship of Taxifolin Derivatives as Anti-inflammatory Agents

HU Chun-ling1,2*,ZHOU Zong-bao2,XIANG Yuan-hang2,PENG Xiao-zhi2,YE Xiao-chuan2,TIAN juan1   

  1. 1Hubei Key Laboratory of Drug Synthesis and Optimization,Jingchu University of Technology,Jingmen 448000,China; 2School of Pharmacy,Hubei University of Traditional Chinese Medicine,Wuhan 430065,China
  • Online:2018-10-31 Published:2018-11-01

Abstract: The 2'-hydroxyl chalcone derivatives 3a~3o were prepared by condensation of 2′-hydroxyhypnone derivatives and phenyl aldehyde derivatives under alkali.After oxidation and hydrolysis,A and /or B-ring substitut-ed taxifolins 4a-4o were obtained.Then C-ring varied taxifolins 4p~4r were synthesized by oxidative hy-drolysis of 2′-azyl chalcone derivatives 3p-3r,which were prepared by method above.19 compounds were synthesized and their structures were confirmed by 1H NMR and 13C NMR.To best of our knowledge,13 of them were unknown in the literature.The anti-inflammatory activity of synthesized compounds was evaluated against RAW264.7 cell in vitro.The preliminary results indicated that 4,4c,4i,4l and 4m showed good anti-inflammatory activity (P<0.001).Structure-activity relationship showed that the 5,7-dihydroxyl substitution located in the A-ring was critical for anti-inflammatory activity.The 4/-fluorine substitution located in the B-ring has excellent influence.The anti-inflammatory activity reduced or disappeared when C-ring was varied.

Key words: taxifolin derivatives, chalcone, anti-inflammatory activity

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