8-氮杂双环[3.2.1]辛烷-3-异噁唑肟类衍生物的合成及其杀线虫活性

doi:10.6023/cjoc201601036

有机化学 ›› 2016, Vol. 36 ›› Issue (4): 760-767.DOI: 10.6023/cjoc201601036 上一篇下一篇

研究论文

8-氮杂双环[3.2.1]辛烷-3-异噁唑肟类衍生物的合成及其杀线虫活性

陆青, 沈巧英, 孙璐, 王佳毅, 宋恭华

华东理工大学药学院上海市化学生物学重点实验室上海 200237

收稿日期:2016-01-17 修回日期:2016-02-29 发布日期:2016-03-11
通讯作者: 宋恭华 E-mail:ghsong@ecust.edu.cn
基金资助:
国家自然科学基金(No.21572060)资助项目.

Synthesis and Nematicidal Activities of 8-Azabicyclo[3.2.1]-octane-3-isoxazole Oxime Derivatives

Lu Qing, Shen Qiaoying, Sun Lu, Wang Jiayi, Song Gonghua

Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China. University of Science and Technology, Shanghai 200237

Received:2016-01-17 Revised:2016-02-29 Published:2016-03-11
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21572060).

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摘要/Abstract

基于具有潜在杀线虫活性的托烷衍生物结构,通过1,3-偶极环加成反应,设计合成了19个未见报道的8-氮杂双环[3.2.1]辛烷-3-异噁唑肟类衍生物,通过¹H NMR,¹³C NMR和高分辨质谱对目标化合物的结构进行表征.初步的生物活性测试表明:在浓度25mg/L下,目标化合物对南方根结线虫表现出良好的抑制活性,活性最好的化合物8-甲基-8-氮杂双环[3.2.1]辛烷-3-酮-O-((3-(4-硝基苯基)-4,5-二氢异噁唑-5-基)甲基)肟(9e)在1mg/L浓度下对根结线虫的抑制率达55.6%.

关键词: 氮杂双环, 杀线剂, 5-羟色胺, 1,3-偶极环加成反应

Based on the potential nematicidal activities of tropane derivatives structure, 19 unreported 8-azabicyclo[3.2.1]- octane-3-isoxazole oxime derivatives were designed and synthesized by 1,3-dipolar cycloaddition reaction. Their structures were confirmed by ¹H NMR, ¹³C NMR and HRMS techniques. Preliminary bioassay results showed that targeted compounds exhibited good nematicidal activities against Meloidogyne incognita at concentration of 25 mg/L, and 8-methyl-8-azabicyclo- [3.2.1]octan-3-one-O-((3-(4-nitrophenyl)-4,5-dihydroisoxazol-5-yl)methyl)oxime (9e) showed the best nematicidal activities with 55.6% at concentration of 1 mg/L.

Key words: 8-azabicyclo, nematicide, serotonin, 1,3-dipolar cycloaddition reaction

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陆青, 沈巧英, 孙璐, 王佳毅, 宋恭华. 8-氮杂双环[3.2.1]辛烷-3-异噁唑肟类衍生物的合成及其杀线虫活性[J]. 有机化学, 2016, 36(4): 760-767.

Lu Qing, Shen Qiaoying, Sun Lu, Wang Jiayi, Song Gonghua. Synthesis and Nematicidal Activities of 8-Azabicyclo[3.2.1]-octane-3-isoxazole Oxime Derivatives[J]. Chin. J. Org. Chem., 2016, 36(4): 760-767.

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8-氮杂双环[3.2.1]辛烷-3-异噁唑肟类衍生物的合成及其杀线虫活性

Synthesis and Nematicidal Activities of 8-Azabicyclo[3.2.1]-octane-3-isoxazole Oxime Derivatives

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