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Chemistry and Industry of Forest Products ›› 2019, Vol. 39 ›› Issue (3): 43-48.doi: 10.3969/j.issn.0253-2417.2019.03.006

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Synthesis and Biological Activity of Isopimaric Furfural Acylhydrazone Derivatives

Yanju LU1,2,3(),Zhendong ZHAO1,2,3,*(),Jing WANG1,2,3,Shichao XU1,2,3,Liangwu BI1,2,3,Yuxiang CHEN1,2,3   

  1. 1. Institute of Chemical Industry of Forest Products, CAF; National Engineering Lab. for Biomass Chemical Utilization; Key Lab. of Chemical Engineering of Forest Products, National Forestry and Grassland Administration; Key Lab. of Biomass Energy and Material, Jiangsu Province, Nanjing 210042, China
    2. Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037, China
    3. Research Institute of Forestry New Technology, CAF, Beijing 100091, China
  • Received:2018-10-29 Online:2019-06-28 Published:2019-06-26
  • Contact: Zhendong ZHAO E-mail:luyanju-1982@163.com;zdzhao@189.cn
  • Supported by:


Hydrazine of isopimaric acid was synthesized by first chlorination then reaction with hydrazine hydrate using isopimaric acid as raw material. A series of novel isopimaric furfural acylhydrazone derivatives such as isopimaric acid 2-furaldehyde acylhydrazone(4a), isopimaric acid(5-methyl-2-furancarboxaldehyde) acylhydrazone(4b), isopimaric acid(5-hydroxymethylfurfural) acylhydrazone(4c), isopimaric acid(5-bromo-2-furaldehyde) acylhydrazone(4d) and isopimaric acid(5-hydroxymethylfurfural) acylhydrazone(4c), isopimaric acid(5-(4-bromopheny) furfural) acylhydrazone(4e) were synthesized by the condensation reactions of furfural with different substituent and intermediate hydrazine of isopimaric acid. The structures of isopimaric furfural acylhydrazone derivatives were characterized and indentified by FT-IR, 1H NMR, 13C NMR and MS. The results showed that most of the target compounds exhibited a certain fungicidal activity on Streptococcus pneumoniae, Klebsiella pneumoniae, Escherichia coli, Staphylococcus epidermidisand and S. aureus, in which the minimal inhibitory concentration(MIC) of 4a against Klebsiella pneumoniae is 1.95 mg/L; the minimal inhibitory concentration(MIC) of 4c against Streptococcus pneumoniae is 0.98 mg/L. Compound 4d had inhibition rate of 75.17%, 82.33%, 78.52% and 80.97% against hepatocarcinoma cells(Hep G2), breast cancer cells(MDA-MB-231), prostate cancer(PC-3), and cervical cancer(Hela) at the concentration of 100 μmol/L; Compound 4e had inhibition rate of 93.68% against Hep G2 at the concentration of 100 μmol/L, indicating that compound 4e had a strong inhibitory activity on human hepatoma cells.

Key words: isopimaric acid, furfural, synthesis, characterization, biological activity

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