Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (9): 2183-2190.DOI: 10.6023/cjoc201603023 Previous Articles     Next Articles



芮坚a, 杨金来a, 黄建峰a, 王佳瑜a, 徐徐a,b,c, 徐海军a, 王石发a,b,c   

  1. a 南京林业大学化学工程学院 南京 210037;
    b 江苏省生物质能源与材料重点实验室 南京 210042;
    c 广西林产化学与工程重点实验室 南宁 530008
  • 收稿日期:2016-03-14 修回日期:2016-04-11 发布日期:2016-05-06
  • 通讯作者: 王石发
  • 基金资助:


Synthesis, Antitumor and Anti-inflammatory Activities of Isolongifolanonyl Pyrazole Derivatives

Rui Jiana, Yang Jianlaia, Huang Jianfenga, Wang Jiayua, Xu Xuaa,b,c, Xu Haijuna, Wang Shifaa,b,c   

  1. a College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037;
    b Key Laboratory of Biomass Energy and Material of Jiangsu Province, Nanjing 210042;
    c Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Nanning 530008
  • Received:2016-03-14 Revised:2016-04-11 Published:2016-05-06
  • Supported by:

    Project supported by the University Science Research Project of Jiangsu Province (No.14KJ220001), the Natural National Science Foundation of China (No.31470529), and the Open Funding of Jiangsu Key Laboratory of Biomass Energy and Materials (No.JSBEM2014010).

A series of new isolongifolanonyl pyrazole derivatives 3a~3j were synthesized by aldol-condensation, cyclization and dehydroaromatization from isolongifolanone. The yields of products ranged from 69.5% to 76.5%. The chemical structures of compounds obtained were elucidated by 1H NMR, 13C NMR, IR, MS spectra and elemental analysis. The strucure of compound 3i was determined by X-ray single crystal diffraction. Their inhibitory activities against human hepatoma cell (HepG2) and human umbilical vein endothelial cell (HUVECs) were evaluated. The results indicated that compounds 3h and 3i[IC50=(15.42±0.6), (4.74±0.3) μmol/L] showed obvious inhibitory activity against HUVECs. Compounds 3a, 3c,3e and 3j[IC50=(5.27±0.5), (6.71±0.4), (4.68±0.2), (4.57±0.5)] μmol/L showed better antitumor activity against HepG2.

Key words: isolongifolanone, 7-arylidene-isolongifolanone, pyrazole derivatives, anti-inflammatory activity, antitumor activity