Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (11): 2978-2984.DOI: 10.6023/cjoc201706029 Previous Articles     Next Articles



李克建a,b, 吴双志a, 王囡囡a, 朱晓磊a, 杨光富a   

  1. a 华中师范大学化学学院 农药与化学生物学教育部重点实验室 武汉 430079;
    b 四川警察学院治安系 泸州 646000
  • 收稿日期:2017-06-21 修回日期:2017-07-10 发布日期:2017-07-18
  • 通讯作者: 朱晓磊, 杨光富;
  • 基金资助:


Design, Synthesis and Bioactivity of New Cyclohexanedione Inhibitors

Li Kejiana,b, Wu Shuangzhia, Wang Nannana, Zhu Xiaoleia, Yang Guangfua   

  1. a Key Laboratory of Pesticide and Chemical Biology, College of Chemistry, Central China Normal University, Wuhan 430079;
    b Department of Public Security, Sichuan Police College, Luzhou, Sichuan 646000
  • Received:2017-06-21 Revised:2017-07-10 Published:2017-07-18
  • Contact: 10.6023/cjoc201706029;
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21472065), the 111 Project (No. B17019) and the Fundamental Research Funds for the Central Universities (No. CCNU15A02013).

Acetyl-CoA carboxylase (ACCase, EC was one of important herbicidal targets. However, the number of resistant weeds targeting to ACCase had risen to the third place among all of herbicidal targets. Therefore, it is of great importance to design new ACCase inhibitors. Herein, based on the crystal structures, aryloxyphenoxypropanotes (APP)-site and cyclohexanedioneoximes (CHD)-site were used to constructing APP+CHD-site, and then thirteen compounds were designed and synthesized. All the newly prepared compounds were characterized by 1H NMR, 13C NMR and HRMS. The molecular docking showed that 2-((4-(2,4-dichlorophenoxy)phenoxy)methyl)-5-(2-(ethylthio)propyl)cyclohexane-1,3-dione (10a) could occupy not only APP-site, but also CHD-site. In addition, based on the herbicidal activity, some compounds showed some inhibition rate upon tested weeds. Most importantly, 5-(2-(ethylthio)propyl)-2-((4-phenoxyphenoxy)methyl)cyclohexane-1,3-dione (10b) showed a wide range of herbicidal spectrum, which could be used to inhibit not only poaceae weeds, but also broadleaf weeds. All these results indicated that this type of compounds worth of the further investigation.

Key words: ACCase, molecular docking, organic synthesis, herbicidal activity