SIOC English
有机化学
高级检索

有机化学 >

2012 , Vol. 32 >Issue 04: 747 - 754

DOI: https://doi.org/10.6023/cjoc1110091

研究论文

Aspernigerin 类似物的合成及生物活性研究

  • 吴清来 ,
  • 李永强 ,
  • 杨新玲 ,
  • 凌云
展开
  • 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

  网络出版日期: 2012-04-24

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.

收起

Synthesis and Bioactivity of Aspernigerin Analogues

  • Wu Qinglai ,
  • Li Yongqiang ,
  • Yang Xinling ,
  • Ling Yun
Expand
  • 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 date: 2011-10-09

  Revised date: 2011-11-16

  Online 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).

Fold

摘要

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

本文引用格式

吴清来 , 李永强 , 杨新玲 , 凌云 . Aspernigerin 类似物的合成及生物活性研究[J]. 有机化学, 2012 , 32(04) : 747 -754 . DOI: 10.6023/cjoc1110091

Abstract

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

参考文献

[1] Shen, L.; Ye, Y.-H.; Wang, X.-T.; Zhu, H.-L.; Xu, C.; Song, Y.-C.; Li, H.; Tan, R.-X. Chem. Eur. J. 2006, 12, 4393.  

[2] Shen, L. Ph.D. Dissertation, Nanjing University, Nanjing, 2006 (in Chinese). (申丽, 博士论文, 南京大学, 南京, 2006.)

[3] Frank, D. P.; Ernest, C.; Robert, B. D.; Warren, K. J. Med. Chem. 1962, 5, 398.  

[4] Sarah, C.; Raymond, H.; Jean-Pierre, H. J. Org. Chem. 2002, 67, 3502.  

[5] Chen, N.-C. Bioassay of Pesticides, Beijing Agricultural University Press, Beijing, 1991, pp. 161～162 (in Chinese). (陈年春, 农药生物测定技术, 北京农业大学出版社, 北京, 1991, pp. 161～162. )

[6] Chong, J. A.; Fanger, C.; Larson, G. R.; Lumma, W. C.; Moran, M. M.; Ripka, A.; Underwood, J. D.; Weigele, M.; Zhen X. G. US 2007213321, 2007 [Chem. Abstr. 2007, 147, 365488].

[7] Wang, Z.-Y.; Wang, C.-Z.; Wang, F.-X.; Yang, J. Chin. J. Pharm. 2005, 36, 261 (in Chinese). (王志远, 王成章, 王福祥, 杨洁, 中国医药工业杂志, 2005, 36, 261.)

[8] Silverman, I. R.; Ali, S. F.; Cohen, D. H.; Lyga, J. W.; Simmons, K. A.; Cullen, T. G. WO 9726252, 1997 [Chem. Abstr. 1997, 127, 176441].

[9] Li, Z.-G.; Huang, R.-Q.; Shao, R.-L.; Ma, J.-A. Chin. J. Synth. Chem. 2000, 8, 130 (in Chinese). (李在国, 黄润秋, 邵瑞链, 马军安, 合成化学, 2000, 8, 130.)

[10] Beth, A. L.; James, M. R.; Thomas, C. S.; Michael, T. S.; Irene, M. M.; Jeffery, D. W. US 2007004750, 2007 [Chem. Abstr. 2007, 146, 121988].  

[11] Li, G.-Y.; Yan, S.-G.; Jiang, S.; Qian, X.-H.; Huang, Q.-C.; Zhang, R. Chin. J. Org. Chem. 2008, 28, 2001. (李刚月, 阎圣刚, 蒋山, 钱旭红, 黄青春, 张蓉, 有机化学, 2008, 28, 2001.)

[12] Cai, M.-Y.; Li, Z.; Fan, F.; Huang, Q.-C.; Shao, X.-S.; Song, G.-H. J. Agric. Food Chem. 2010, 58, 2624.  
Options
文章导航

/

〈 〉