Synthesis and Insecticidal Evaluation of Neonicotinoid Analogues with Bicyclic Ring System

doi:10.6023/cjoc201308033

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (2): 409-413.DOI: 10.6023/cjoc201308033 Previous Articles Next Articles

Notes

新型双环新烟碱类似物的合成及其生物活性

陈寅波, 范杰, 夏爽, 程家高, 徐晓勇, 李忠

上海市化学生物学重点实验室华东理工大学药学院上海 200237

收稿日期:2013-08-26 修回日期:2013-09-25 发布日期:2013-10-28
通讯作者: 李忠 E-mail:lizhong@ecust.edu.cn
基金资助:
国家重点基础研究发展计划（973计划，No.2010CB126100）、国家高技术研究发展计划（863计划，No.2011AA10A207）、“十一五”国家科技支撑计划（No.2011BAE06B01）和国家自然科学基金（No.21272071）资助项目.

Synthesis and Insecticidal Evaluation of Neonicotinoid Analogues with Bicyclic Ring System

Chen Yinbo, Fan Jie, Xia Shuang, Cheng Jiagao, Xu Xiaoyong, Li Zhong

Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237

Received:2013-08-26 Revised:2013-09-25 Published:2013-10-28
Supported by:
Project supported by the National Basic Research Program of China (973 Program, No. 2010CB126100), the National High Technology Research and Development Program of China (863 Program, No. 2011AA10A207), the National Key Technology R&D Program of China (No. 2011BAE06B01) and the National Natural Science Foundation of China (No. 21272071).

Six novel neonicotinoid analogues with bicyclic ring system were designed and synthesized, and their structures were characterized by ¹H NMR, ¹³C NMR, HRMS and single crystal X-ray diffraction analysis. Preliminary bioassays showed that five target compounds 6a, 6c～6f exhibited good insecticidal activities against cowpea aphids (Aphis craccivora) at 500 mg·L^-1. Docking study was applied to investigate the effect of the bicyclic ring system of the target compound 6a on the biological activity, and compared with mode of action of imidacloprid (IMI) and compound 6a. It was found that the only π-π stacking interaction was found between the plane of pyridine of the target compounds 6a and the aromatic side chain of Tyr 147, which was different binding mode with that of IMI.

Key words: neonicotinoid analogue, synthesis, bioactivity, crystal structure, molecular docking

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Chen Yinbo, Fan Jie, Xia Shuang, Cheng Jiagao, Xu Xiaoyong, Li Zhong. Synthesis and Insecticidal Evaluation of Neonicotinoid Analogues with Bicyclic Ring System[J]. Chin. J. Org. Chem., 2014, 34(2): 409-413.

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新型双环新烟碱类似物的合成及其生物活性

Synthesis and Insecticidal Evaluation of Neonicotinoid Analogues with Bicyclic Ring System

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