有机化学 ›› 2012, Vol. 32 ›› Issue (04): 747-754.DOI: 10.6023/cjoc1110091 上一篇    下一篇

研究论文

Aspernigerin 类似物的合成及生物活性研究

吴清来a, 李永强b, 杨新玲a, 凌云a   

  1. a 中国农业大学理学院应用化学系 农业部农药化学与应用重点开放实验室 北京 100193;
    b 南开大学元素有机化学国家重点实验室 天津 300071
  • 收稿日期:2011-10-09 修回日期:2011-11-16 出版日期:2012-04-25 发布日期:2012-04-24
  • 通讯作者: 凌云 E-mail:lyun@cau.edu.cn
  • 基金资助:

    国家自然科学基金(No. 21072222)和国家973 计划(No. 2010CB126104)资助项目.

Synthesis and Bioactivity of Aspernigerin Analogues

Wu Qinglaia, Li Yongqiangb, Yang Xinlinga, Ling Yuna   

  1. a Key Laboratory of Pesticide Chemistry and Application, Ministry of Agriculture, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193;
    b State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071
  • Received:2011-10-09 Revised:2011-11-16 Online:2012-04-25 Published:2012-04-24
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21072222) and the National Basic Research Program of China (973 Program, No. 2010CB126104).

以天然产物Aspernigerin 为先导, 将Aspernigerin 结构中的一个1,2,3,4-四氢喹啉基团以芳胺类化合物替代, 设计合成了15 个未见文献报道的Aspernigerin 类似物, 结构均经过1H NMR, IR 和元素分析确证. 初步生物活性测试表明,大部分目标化合物均表现出了一定的杀虫和杀菌活性, 其中化合物2n 在200 μg/mL 的浓度下对小菜蛾仍表现出100%的杀虫活性, 优于先导Aspernigerin和对照药剂噻虫嗪; 化合物2d, 2e, 2j, 2k表现出对黄瓜灰霉病优于先导Aspernigerin的抑制活性.

关键词: Aspernigerin, 类似物, 合成, 1,2,3,4-四氢喹啉, 芳胺, 生物活性

Using natural product aspernigerin as the lead compound, fifteen new compounds were designed and synthesized by replaced one 1,2,3,4-tetrahydroquinoline group of aspernigerin with aromatic amine. Those structures were confirmed by 1H NMR, IR spectra and elemental analysis. The preliminary bioassay showed that most of the compounds exhibited certain fungicidal activities and insecticidal activities. In particular, compound 2n showed the most potent bioactivity against Plutella xylostella with the rate of 100% at the concentration of 200 μg/mL, better than aspernigerin and commercial insecticide thiamethoxam, and compounds 2d, 2e, 2j, 2k showed higher inhibition effects against Botrytis cinerea than aspernigerin.

Key words: aspernigerin, analogues, synthesis, 1,2,3,4-tetrahydroquinoline, aromatic amine, bioactivity