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
收藏
页码：1865 / 1880
页数：16
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