Citation: Zhang Qiangjian, Wang Yunyun, Zhao Yuxun, Ma Chonghui, Yang Yiqing, Xu Xu, Gu Wen, Wang Shifa. Synthesis and α-Amylase Inhibitory Potential and Molecular Docking Study of Nopinone-Based Thiazolylhydrazone Derivatives[J]. Chinese Journal of Organic Chemistry, ;2019, 39(5): 1372-1382. doi: 10.6023/cjoc201812032 shu

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

Zhang Qiangjian ^a ,
Wang Yunyun ^a ,
Zhao Yuxun ^a ,
Ma Chonghui ^a ,
Yang Yiqing ^b,c ,
Xu Xu ^a,c ,
Gu Wen ^a,c ,
Wang Shifa ^a,c,,

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

Corresponding author: Wang Shifa, wangshifa65@163.com
Received Date: 19 December 2018
Revised Date: 14 January 2019
Available Online: 19 May 2019
Fund Project: the National Natural Science Foundation of China 31470592Project supported by the National Natural Science Foundation of China (No. 31470592)

Figures(4)

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.
- nopinone,
- thiazolylhydrazone,
- α-amylase inhibitor,
- molecular docking
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