NOVEL NITENPYRAM ANALOGUES WITH TETRAHYDROPYRIDONE-FIXED CIS-CONFIGURATION: SYNTHESIS, INSECTICIDAL ACTIVITIES, AND MOLECULAR DOCKING STUDIES

被引：5

作者：

Sun, Chuan-Wen ^{[1
]}

Wang, Jing ^{[1
]}

Wu, Ying ^{[1
]}

Nan, Shi-Bin ^{[1
]}

Zhang, Wang-Geng

机构：

[1] Shanghai Normal Univ, Coll Life & Environm Sci, Shanghai 200234, Peoples R China

来源：

HETEROCYCLES | 2013年 / 87卷 / 09期

基金：

中国国家自然科学基金;

关键词：

Nitenpyram Analogue; Synthesis; Insecticidal Acvitity; cis-Configuration; Molecular Docking; NITROMETHYLENE NEONICOTINOIDS; CROSS-RESISTANCE; MELDRUMS ACID; DIVERSITY; MECHANISMS; MOTH;

D O I：

10.3987/COM-13-12766

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

To make further researches on the diversity of nitenpyram analogues with a cis-nitromethylene configuration, a series of cis-nitenpyram analogues (3a-q) with tetrahydropyridone-fixed cis-configuration were designed and synthesized. Preliminary bioassays showed that most of the designed nitenpyram analogues exhibited good insecticidal activity at 100 mg/L against Nilaparvata lugens and Myzus persicae, while analogues 3n afforded the best in vitro activity. Modeling the ligand-receptor complexes by molecular docking study revealed the analogues 3 with various substituents on phenyl show their different binding affinities to the insect nAChR, which also explained the structure-activity relationships observed in vitro.

引用

页码：1865 / 1880

页数：16

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