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Chemistry and Industry of Forest Products ›› 2023, Vol. 43 ›› Issue (1): 43-50.doi: 10.3969/j.issn.0253-2417.2023.01.005

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Synthesis of Carbamates and Their AChE Inhibitory Activity

Jing WANG1,2,3, Yuxiang CHEN1,3, Shengnan LI1, Hongmei ZHANG1,2, Jianxin JIANG2, Zhendong ZHAO1,*()   

  1. 1. Institute of Chemical Industry of Forest Products, CAF; Key Lab. of Biomass Energy and Material, Jiangsu Province; Key Lab. of Chemical Engineering of Forest Products, National Forestry and Grassland Administration; National Engineering Research Center of Low-Carbon Processing and Utilization of Forest Biomass; Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing 210042, China
    2. College of Materials Science and Technology, Beijing Forestry University, Beijing 100083, China
    3. Research Institute of Forestry New Technology, CAF, Beijing 100091, China
  • Received:2021-11-03 Online:2023-02-28 Published:2023-02-28
  • Contact: Zhendong ZHAO E-mail:zdzhao@189.cn


Using 3-carene, a major component of turpentine, as the raw material, 3-isopropyl-5-cresol(1) and carvacrol(2) were first synthesized, and then 14 carbamate compounds containing isopropyl cresol structure were further prepared by their reactions with isocyanates(method A) or carbamoyl chlorides(method B). The acetylcholinesterase(AChE) inhibitory activities for all synthetic compounds were studied. The research results showed that the reaction of phenolic compounds with isocyanates was an efficient synthesis process for the preparation of carbamates. The larger N-substituent structure in the isocyanate, the easier reaction occurs, and the molar yield of aryl substitution products could reach more than 90%. In terms of AChE inhibition, the activities of 3-isopropyl-5-cresol derivatives were generally higher than those of carvacrol derivatives. The activities of N-aliphatic substituted products were significantly higher than those of N-aryl substituted products, and the activities of short-chain aliphatic substituted products were higher than those of long-chain aliphatic and cycloaliphatic groups substituted products. The N-methyl substituted product of 3-isopropyl-5-cresol showed the excellent AChE inhibitory activity of 90.5% against Huperzine A and surpassed the positive control Listigmine(89.6%), which was a commercial AChE inhibitor with carbamate. The activity of N, N-dimethyl substituted product of 3-isopropyl-5-cresol was evidently higher than its N-methyl substituted product, whose inhibition efficiency reached 97.9% of Huperzine A. The relationship between the concentration and the inhibition rate showed that 3-isopropyl-5-methylphenyl-N, N-dimethylcarbamate(Ⅰ-2) had a substantially equivalent AChE inhibitory activity to Huperzine A when the concentration was greater than 1.25 mmol/L, indicating that it had the potential to be developed as a therapeutic drug for Alzheimer's disease or insecticide.

Key words: turpentine, 3-carene, carbamate, acetylcholinesterase inhibitor, 3-isopropyl-5-methylphenyl-N, N-dimethylcarbamate

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