Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (04): 747-754.DOI: 10.6023/cjoc1110091 Previous Articles     Next Articles

Articles

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 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 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).

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