Multistep Synthesis and Nematicidal Activity of 2-(8-azabicyclo[3.2.1]octan-3-yl)-3-imino-2,3-dihydro-1H-isoindol-1-One Derivatives

被引：1
|
作者：
Xu, Jun [1 ]
Yang, Tianjiao [1 ]
Wang, Jiayi [1 ]
Song, Gonghua [1 ]
机构：
[1] East China Univ Sci & Technol, Sch Pharm, 130 Meilong Rd, Shanghai 200237, Peoples R China
来源：
CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2021年 / 57卷 / 01期
基金：
中国国家自然科学基金;
关键词：
azabicyclo; iminoisoindoline; isocyanide insertion; nematicidal activity; NEMATODES; 5-HT3;
D O I：
10.1007/s10593-021-02864-z
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Novel 2-(8-azabicyclo[3.2.1]octan-3-yl)-3-imino-2,3-dihydro-1H-isoindol-1-ones derived from 5-HT3 receptor antagonists hexahydroazepinylbenzamides were designed and synthesized through isocyanide insertion reaction. All target compounds were evaluated against pinewood nematodes B. xylophilus and root-knot nematodes M. incognita. Good lethal rate (75%) for 3-(tert-butylimino)-5-chloro-2-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-2,3-dihydro-1H-isoindol-1-one and serious nervous curl effect against pinewood nematodes B. xylophilus for 3-(tert-butylimino)-2-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-2,3-dihydro-1H-isoindol-1-one were observed at 10 mg/l. The inhibition activities of 3-[(4-methoxyphenyl)imino]-2-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-2,3-dihydro-1H-isoindol-1-one against root-knot nematodes M. incognita were 84% at 160 mg/l and 60% at 20 mg/l for in vitro test and test tube test, respectively.
引用
收藏
页码：31 / 39
页数：9
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