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

Chemical Research in Chinese Universities ›› 2014, Vol. 30 ›› Issue (6): 931-936.doi: 10.1007/s40242-014-4191-y

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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).

Abstract

Abstract:

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.

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]. Chemical Research in Chinese Universities, 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

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