Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (07): 1043-1048. Previous Articles     Next Articles

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灯盏乙素苷元4-N-取代氨甲基苯甲酸酯的合成及体外抗氧化活性研究

傅晓钟,邢凤晶,蓝燕宇,王爱民,王永林*,李靖,周雯,张伟,刘影   

  1. (贵阳医学院药学院 贵阳 550004)
  • 收稿日期:2010-12-21 修回日期:2011-01-27 发布日期:2011-02-23
  • 通讯作者: 王永林 E-mail:Ylwang_gmc@163.com

Synthesis and in vitro Anti-oxidative Activity Studies of 4-N-Subs- tituted-aminomethyl-benzoate Derivatives of Scutellarein

FU Xiao-Zhong, XING Feng-Jing, Lan Yan-Yu , WANG Ai-Min, WANG Yong-Lin, LI Jing, ZHOU Wen, ZHANG Wei, LIU Ying   

  1. (School of Pharmacy, Guiyang Medical College, Guiyang 550004)
  • Received:2010-12-21 Revised:2011-01-27 Published:2011-02-23

To synthesize scutellarein derivatives with improved neuroprotective activity, six 4-N-substi- tuted-aminomethyl-benzoate derivatives of scutellarein were prepared in the presence of N,N-dicyclo- hexylcarbodiimide (DCC)/4-dimethylaminopyridine (DMAP) with scutellarein and N-substituted-aminomethyl-benzoic acid as starting materials. The structures of the compounds 6a6f were established by 1H NMR, ESI-MS and HRMS techniques. The synthesized compounds were assayed by their physicochemical properties and in vitro anti-oxidative activity against H2O2 induced oxidative damage in PC12 cells. The results showed that all the compounds had potent anti-oxidative activity by reducing lactate dehydrogenase (LDH) level in concentration-dependent manner, compounds 6c and 6e have more potent anti-oxidative activity than positive control VE with LDH release rate (36.83±1.78)% and (36.69±1.68)% at 20 μmol•L-1 concentration. Primary structure-activity relationship revealed that compounds with N atom of (aminomethyl)benzoic acid involved in the formation of 1,4-bis-heterocyclic would have more potent anti-oxidative activity.

Key words: scutellarein, PC12 cells, anti-oxidative activity, aminomethyl-benzoic acid