Design, Synthesis and Bioactivity of New Cyclohexanedione Inhibitors

doi:10.6023/cjoc201706029

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

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新型环己二酮类抑制剂的设计、合成及其生物活性研究

李克建^a,b, 吴双志^a, 王囡囡^a, 朱晓磊^a, 杨光富^a

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 E-mail:xlzhu@mail.ccnu.edu.cn;gfyang@mail.ccnu.edu.cn
基金资助:
国家自然科学基金（Nos.21772057，21472065）、高等学校学科创新引智计划（No.B17019）和中央高校基本科研业务费（No.CCNU15A02013）.

Design, Synthesis and Bioactivity of New Cyclohexanedione Inhibitors

Li Kejian^a,b, Wu Shuangzhi^a, Wang Nannan^a, Zhu Xiaolei^a, Yang Guangfu^a

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 E-mail:xlzhu@mail.ccnu.edu.cn;gfyang@mail.ccnu.edu.cn
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).

1. Design, Synthesis and Bioactivity of New Cyclohexanedione Inhibitors.PDF(6194KB)

Abstract

Acetyl-CoA carboxylase (ACCase, EC 6.4.1.2) 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

Cite this article

Li Kejian, Wu Shuangzhi, Wang Nannan, Zhu Xiaolei, Yang Guangfu. Design, Synthesis and Bioactivity of New Cyclohexanedione Inhibitors[J]. Chin. J. Org. Chem., 2017, 37(11): 2978-2984.

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新型环己二酮类抑制剂的设计、合成及其生物活性研究

Design, Synthesis and Bioactivity of New Cyclohexanedione Inhibitors

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