Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (5): 1372-1382.DOI: 10.6023/cjoc201812032 Previous Articles     Next Articles



张强健a, 王芸芸a, 赵雨珣a, 马崇慧a, 杨益琴b,c, 徐徐a,c, 谷文a,c, 王石发a,c   

  1. a 南京林业大学化学工程学院 南京 210037;
    b 南京林业大学轻工与食品学院 南京 210037;
    c 南京林业大学林业资源高效加工利用协同创新中心 南京 210037
  • 收稿日期:2018-12-19 修回日期:2019-01-14 发布日期:2019-02-19
  • 通讯作者: 王石发
  • 基金资助:


Synthesis and α-Amylase Inhibitory Potential and Molecular Docking Study of Nopinone-Based Thiazolylhydrazone Derivatives

Zhang Qiangjiana, Wang Yunyuna, Zhao Yuxuna, Ma Chonghuia, Yang Yiqingb,c, Xu Xua,c, Gu Wena,c, Wang Shifaa,c   

  1. a College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037;
    b College of Light Industry and Food, Nanjing Forestry University, Nanjing 210037;
    c Co-innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037
  • Received:2018-12-19 Revised:2019-01-14 Published:2019-02-19
  • Contact: 10.6023/cjoc201812032
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 31470592).

A series of nopinone-based thiazolyhydrazone derivatives were synthesized by using nopinone derivated from natural β-pinene as the starting material in three steps, including aldol reaction with aromatic aldehydes, condensation with aminothiourea, and cyclization with bromoacetophenone. The structures of synthesized compounds were characterized by 1H NMR, 13C NMR and HRMS. α-Amylase inhibitory activities of these compounds were also investigated. The results showed that 6 compounds among them had good inhibitory activities compared with the positive control acarbose. Especially, 4-(2-(2-(6,6-dimethyl-3-(4-methylbenzylidene))bicyclo[3.1.1]heptane-2-ylidene)indolyl-4-thiazol-4-yl)phenol (SZ14) exhibited remarkable α-amylase inhibitory activity with IC50 value of 4.11 μmol/L. From the structure-activity relationship, the structure of R2 gave great influence on the activities of thiazolyhydrazone derivatives. The kinetic inhibition study revealed that those 6 compounds were the noncompetitive inhibitor against α-amylase. It was used for molecular docking study to find out binding affinities for thiazolylhydrazone derivatives, and the binding mode of compound SZ14 with α-amylase was primarily investigated with molecular docking method.

Key words: nopinone, thiazolylhydrazone, α-amylase inhibitor, molecular docking