SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

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

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

Articles

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

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

Cite this article

Wu Qinglai , Li Yongqiang , Yang Xinling , Ling Yun . Synthesis and Bioactivity of Aspernigerin Analogues[J]. Chinese Journal of Organic Chemistry, 2012 , 32(04) : 747 -754 . DOI: 10.6023/cjoc1110091

References

[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
Outlines

/

〈 〉