Synthesis, Insecticidal Activities and Molecular Docking Studies on cis-Nitenpyram Analogues with a Flexible Amido Segment Anchored on Tetrahydropyrimidine Ring

doi:10.1007/s40242-014-4191-y

高等学校化学研究 ›› 2014, Vol. 30 ›› Issue (6): 931-936.doi: 10.1007/s40242-014-4191-y

Synthesis, Insecticidal Activities and Molecular Docking Studies on cis-Nitenpyram Analogues with a Flexible Amido Segment Anchored on Tetrahydropyrimidine Ring

FANG Ting^1,3, SUN Chuanwen¹, XU Yiyi¹, YUAN Jing¹, WANG Yuanfeng¹, XING Jiahua²

1. College of Life and Environment Sciences, Shanghai Normal University, Shanghai 200234, P. R. China;
2. Bioassay Department, Branch of National Pesticide R&D South Center, Hangzhou 310023, P. R. China;
3. Patent Examination Cooperation Jiangsu Center of the Patent Office, SIPO, Suzhou 215011, P. R. China

收稿日期:2014-05-16 修回日期:2014-06-23 出版日期:2014-12-01 发布日期:2014-09-22
通讯作者: SUN Chuanwen E-mail:willin@shnu.edu.cn
基金资助:
Supported by the Key Scientific “Twelfth Five-Year” National Technology Support Program of China(No.2011BAE06B01- 17).

Synthesis, Insecticidal Activities and Molecular Docking Studies on cis-Nitenpyram Analogues with a Flexible Amido Segment Anchored on Tetrahydropyrimidine Ring

FANG Ting^1,3, SUN Chuanwen¹, XU Yiyi¹, YUAN Jing¹, WANG Yuanfeng¹, XING Jiahua²

1. College of Life and Environment Sciences, Shanghai Normal University, Shanghai 200234, P. R. China;
2. Bioassay Department, Branch of National Pesticide R&D South Center, Hangzhou 310023, P. R. China;
3. Patent Examination Cooperation Jiangsu Center of the Patent Office, SIPO, Suzhou 215011, P. R. China

Received:2014-05-16 Revised:2014-06-23 Online:2014-12-01 Published:2014-09-22
Contact: SUN Chuanwen E-mail:willin@shnu.edu.cn
Supported by:
Supported by the Key Scientific “Twelfth Five-Year” National Technology Support Program of China(No.2011BAE06B01- 17).

摘要/Abstract

摘要：

To make further studies on the difference of cis-nitenpyram analogues, a series of cis-nitenpyram compounds containing a flexible amido segment anchored on tetrahydropyrimidine ring was designed and synthesized. Preliminary bioassays indicate that all the analogues exhibit a mortality of 100% at 100 mg/L, and the analogue 4d shows the best activity against Nilaparvata lugens and Myzus persicae, with a mortality of 100% at 4 mg/L (LC₅₀=0.172 mg/L). The structure activity relationship studies show that insecticidal activities of the analogues are affected by the kinds and size of substituent R. In addition, the molecular docking simulations reveal that compouds 4 with a flexible amido segment on tetrahydropyrimidine ring show their different binding affinities for the nicotinic acetylcholine receptor(nAChR) of insect and compoud 4d shows stronger hydrogen-bonding with nAChR, which may provide the structure-activity relationship observed in vitro.

关键词: cis-Nitenpyram analogue, Nicotinic acetylcholine receptor(nAChR), Flexible amido segment, Hydrogen-bonding action, Structure activity relationship, Insecticidal activity, Molecular docking

Abstract:

Key words: cis-Nitenpyram analogue, Nicotinic acetylcholine receptor(nAChR), Flexible amido segment, Hydrogen-bonding action, Structure activity relationship, Insecticidal activity, Molecular docking

FANG Ting, SUN Chuanwen, XU Yiyi, YUAN Jing, WANG Yuanfeng, XING Jiahua. Synthesis, Insecticidal Activities and Molecular Docking Studies on cis-Nitenpyram Analogues with a Flexible Amido Segment Anchored on Tetrahydropyrimidine Ring[J]. 高等学校化学研究, 2014, 30(6): 931-936.

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Synthesis, Insecticidal Activities and Molecular Docking Studies on cis-Nitenpyram Analogues with a Flexible Amido Segment Anchored on Tetrahydropyrimidine Ring

Synthesis, Insecticidal Activities and Molecular Docking Studies on cis-Nitenpyram Analogues with a Flexible Amido Segment Anchored on Tetrahydropyrimidine Ring

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