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Synthesis of Substituted Phenylpropyl Aldehyde Thiosemicarbazone Compounds and Their Bioactivity on Tyrosinase of Cotton Bollworm

  • Xu Yan ,
  • Wang zhen ,
  • Ling Yun ,
  • Dong Wei ,
  • Xing Jing ,
  • Liang Pei ,
  • Yang Xinling
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  • a Key Laboratory of Pesticide Chemistry and Application, Ministry of Agriculture, College of Science, China Agricultural University, Beijing 100193;
    b College of Agriculture and Biotechnology, China Agricultural University, Beijing 100193

Received date: 2011-11-18

  Revised date: 2011-12-17

  Online published: 2012-03-22

Supported by

Project supported by the National Scientific and Technology Supporting Program of China (No. 2011BAE06B05-5), the National Key Project for Basic Research (No. 2010CB126104) and the National High Technology Research and Development Program (No. 2006AA10A201).

Abstract

Tyrosinase played an important biological function in insect and might be a potent target for pest control. In order to find new lead of pesticide, a series of substituted phenylpropyl aldehyde thiosemicarbazone compounds were designed based on our previous work. The title compounds were synthesized from the starting material of substituted benzaldehyde in 5 steps. Their structures were characterized by IR, 1H NMR, MS and EA. The bioassay result showed that all of the title compounds exhibited higher inhibitory effect than commercial reagent tropolone on the tyrosinase of cotton bollworm, Helicoverpa armigera.

Cite this article

Xu Yan , Wang zhen , Ling Yun , Dong Wei , Xing Jing , Liang Pei , Yang Xinling . Synthesis of Substituted Phenylpropyl Aldehyde Thiosemicarbazone Compounds and Their Bioactivity on Tyrosinase of Cotton Bollworm[J]. Chinese Journal of Organic Chemistry, 2012 , 32(07) : 1278 -1283 . DOI: 10.6023/cjoc1111181

References

[1] Kim Y. J.; Uyama H. Cell. Mol. Life Sci. 2005, 62, 1707.  
[2] Thomas K.; Christoph E.; James C. S.; Bernt K. Nat. Struct. Biol. 1998, 5, 1084.  

[3] Liu C.-Y.; Gao X.-W.; Liang P.; Tang F. Chin. J. Pestic. 2004, 43, 497.(in Chinese) (刘春艳,高希武,梁沛,汤芳,农药, 2004, 43, 497.)
[4] Xue C.-B.; Zhang L.; Luo W.-C.; Xie X.-Y.; Jiang L.; Xiao T. Bioorg. Med. Chem. 2007, 15, 2006.  
[5] Liu J.-B.; Yi W.; Wan Y.-Q. Bioorg. Med. Chem. 2008, 16, 1096.  
[6] a). Liu J.-B.; Cao R.-H.; Yi W.; Ma C.-M.; Wan Y.-Q.; Zhou B.-H.; Ma L.; Song H.-C.. Bioorg. Eur. J. Med. Chem. 2009, 44, 1773.; b) Yi W.; Cao R.-H.; Wen H.; Yan Q.; Zhou B.-H.; Ma L.; Song H.-C.. Bioorg. Med. Chem. Lett. 2009, 19, 6157.  
[7] Ramadan, El S. Chin. J. Chem. 2010, 28, 594.
[8] Wang Z.; Xu Y.; Dong W.; Liang P.; Yang X.-L. Chin. J. Org. Chem. 2011, 31, 567.(in Chinese) (王振, 徐焱,董玮,梁沛,杨新玲,有机化学,2011, 31, 567.)
[9] Wang Z.; Dong W.; Xu Y.; Liang P.; Yang X.-L. Chin. J. Pestic. Sci. 2010, 12, 264.(in Chinese) (王振,董玮,徐焱,梁沛,杨新玲,农药学学报,2010, 12, 264.)
[10] Yang S.-X.; Kang T.-N.; Yang X.-L.; Sun Y.-F.; Rui C.-H; Ling Y. Chin. J. Org. Chem. 2010, 12, 1870.(in Chinese) (杨绍祥,康铁牛,杨新玲,孙玉凤,芮昌辉,凌 云,有机化学,2010, 12, 1870)
[11] Kumar, D.; Sandhu, J. S. Syn. Comm. 2010, 40, 1915.  
[12] Kumar, B.; Verma, R. K. Syn. Comm. 1984, 14, 1359.  
[13] Enzo S.; Patrizia F.; Piero S. J. Org. Chem. 1981, 46, 4584.  
[14] Carolina, M. D.; Hugo, V.; Joao, X. A. Eu. J. Pharm. Sci. 2004, 23, 363.
[15] Liu W.-W.; Zhao Y.-Q.; Wang Q.-Q.; Li N.; Tang L.-J.; Zeng Y.-X. Chin. J. Org. Chem. 2008, 28, 907. (刘玮炜, 赵跃强, 王钦琪, 李娜, 唐丽娟, 曾艳霞, 有机化学,2008, 28, 907.(in Chinese)
[16] Ishaaya, I. Pestic. Biochem. Physiol. 1974, 4, 484.  
[17] Balasubramanian N.; Deepak B.; Devayani P.; Vishnukant M.; Avinash D. Eur. J. Med. Chem. 2004, 39, 827.
[18] Tanuma, S.; Yoshimori, A.; Takahashi, A.; Ebizuka, S.; Kamiya, T.; Takeuchi, S. JP 2010006732, 2010. [Chem. Abstr. 2010, 144, 462613].
[19] Ley J. P.; Bertram H. J. Bioorg. Med. Chem. 2001, 9, 1879.  
[20] Wangsa T. I.; Henriette J. R.; Amrah W.; Jurriaan J. M.; Fabrizia F.; Harry J. W.; Bauke W. D. Biochem. 2011, 50, 5477.  
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