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Chemistry and Industry of Forest Products ›› 2018, Vol. 38 ›› Issue (6): 117-123.doi: 10.3969/j.issn.0253-2417.2018.06.016

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Synthesis and Anticancer Activity of Dehydroabietyl Primary Amine Derivatives

QI Zhiwen1,2, WANG Chengzhang1, JIANG Jianxin2   

  1. 1. Institute of Chemical Industry of Forest Products, CAF;National Engineering Lab. for Biomass Chemical Utilization;Key and open Lab. of Forest Chemical Engineering, SFA;Key Lab. of Biomass Energy and Material, Jiangsu Province, Nanjing 210042, China;
    2. College of Materials Science and Technology, Beijing Forestry University, Beijing 100083, China
  • Received:2018-05-16 Online:2018-12-25 Published:2018-12-27

Abstract: The primary amine derivatives of dehydroabietic acid:dehydroabietic amide formic acid (1), dehydroabietic amide acetic acid (2), dehydroabietic amide propionic acid (3) and dehydroabietic amide butyric acid (4) were synthesized by a simple and efficient one-pot method with levopimaric acid (0.3 mmol) as raw material, triethylamine (TEA) as base, 1-(3-dimethylamino propyl)-3-ethyl carbodiimide hydrochloride (EDCI) as dehydrant, 1H benzotriazole-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate/4-dimethylamino pyridine (n(PyBOP):n(DMAP)=0.03 mmol:0.01 mmol) as catalyst and acetonitrile as solvent. The yield of the compound 3 were up to 78%. The compound 3 modified by primary amine had a high proliferation inhibitory activity toward human gastric cancer MKN-45 cell line with the IC50 of 31.26 μmol/L.

Key words: levopimaric acid, dehydroabietic acid, carboxyl group, steric resistance, primary amine, amidation

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