SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2017 , Vol. 37 >Issue 8: 2044 - 2049

DOI: https://doi.org/10.6023/cjoc201702003

ARTICLE

Design, Synthesis, Fungicidal Activity and Docking Study of Acyl Urea Derivatives Containing Pyrazole Moiety

  • Sun Nabo ,
  • Shen Zhonghu ,
  • Zhai Zhiwen ,
  • Wu Hongke ,
  • Weng Jianquan ,
  • Tan Chengxia ,
  • Liu Xinghai
Expand
  • a College of Biology and Environmental Engineering, Zhejiang Shuren University, Hangzhou 310015;
    b College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Received date: 2017-02-03

  Revised date: 2017-03-30

  Online published: 2017-04-18

Supported by

Project supported by the National Natural Science Foundation of China (No. 31401691) and the Zhejiang Provincial Natural Science Foundation of China (No. LY16C14007).

Fold

Abstract

A series of novel acyl urea derivatives containing pyrazole moiety were synthesized from ethyl acetoacetate, triethyl orthoformate, methylhydrazine by multi-step reactions. Their structures were characterized by 1H NMR and HRMS spectra. The target compounds were evaluated for their fungicidal activity. The results indicated that some of the title compounds displayed certain fungicidal activities against Cercospora arachidicola, Sclerotinia sclerotiorum, Rhizoctonia solani and Physalopora piricola. The docking results indicated the hydrogen bond formed between the amide group and Ser 39 residue.

Key words： pyrazole; acyl urea; synthesis; fungicidal activity; docking

Cite this article

Sun Nabo , Shen Zhonghu , Zhai Zhiwen , Wu Hongke , Weng Jianquan , Tan Chengxia , Liu Xinghai . Design, Synthesis, Fungicidal Activity and Docking Study of Acyl Urea Derivatives Containing Pyrazole Moiety[J]. Chinese Journal of Organic Chemistry, 2017 , 37(8) : 2044 -2049 . DOI: 10.6023/cjoc201702003

References

[1] Russell, P. E. Outlooks Pest Manage. 2009, 20, 122.
[2] Mu, J. X.; Shi, Y. X.; Yang, M. Y.; Sun, Z. H.; Liu, X. H.; Li, B. J.; Sun, N. B. Molecules 2016, 21, 68.
[3] Elebe, H.; Rieck, H.; Dunkel, R. WO 02008195, 2002[Chem. Abstr. 2002, 136, 151162].
[4] Elebe, H.; Rieck, H.; Dunkel, R. WO 03010149, 2003[Chem. Abstr. 2003, 138, 137308].
[5] Du, S.; Tian, Z.; Yang, D.; Li, X.; Li, H.; Jia, C.; Che, C.; Wang, M.; Qin, Z. Molecules 2015, 20, 8395.
[6] Chen, W.; Wei, W.; Wu, C. C.; Li, Y. X.; Li, Y. H.; Yu, S. J.; Li, Z. M. Chin. J. Org. Chem. 2015, 35, 1576(in Chinese) (陈伟, 魏巍, 吴长春, 李玉新, 李永红, 于淑晶, 李正名, 有机化学, 2015, 35, 1576.)
[7] Chen, Y. W.; Wan, Y. Y.; Liu, Q. X.; Liu, J. B.; Xiong, L. X.; Yu, S. J.; Li, Z. M. Chin. J. Org. Chem. 2015, 35, 882(in Chinese) (陈有为, 万莹莹, 刘巧霞, 刘敬波, 熊丽霞, 于淑晶, 李正名, 有机化学, 2015, 35, 882.)
[8] Li, C. K.; Jiang, L.; Wang, Y.; Wan, F. X.; Zhang, P. Z.; Li, Y.; Cui, Z. N. Chin. J. Org. Chem. 2014, 34, 2296(in Chinese) (李成坤, 姜林, 王悦, 万福贤, 张沛之, 李映, 崔紫宁, 有机化学, 2014, 34, 2296.)
[9] Liu, X. H.; Wang, Q.; Sun, Z. H.; Wedge, D. E.; Becnel, J. J.; Estep, A. S.; Tan, C. X.; Weng, J. Q. Pest Manage. Sci. 2017, 73, 953.
[10] Chen, J. N.; Wang, X. F.; Li, T.; Wu, D. W.; Fu, X. B.; Zhang, G. J.; Shen, X. C.; Wang, H. S. Eur. J. Med. Chem. 2016, 107, 12.
[11] Liu, X. H.; Zhao, W.; Shen, Z. H.; Xing, J. H.; Yuan, J.; Yang, G.; Xu, T. M.; Peng, W. L. Bioorg. Med. Chem. Lett. 2016, 26, 3626
[12] Zhao, W.; Xing, J. H.; Xu, T. M.; Peng, W. L.; Liu, X. H. Front. Chem. Sci. Eng. 2017, 11, 363.
[13] Liu, X. H.; Zhai, Z. W.; Xu, X. Y.; Yang, M. Y.; Sun, Z. H.; Weng, J. Q.; Tan, C. X.; Chen, J. Bioorg. Med. Chem. Lett. 2015, 25, 5524.
[14] Zhai, Z. W.; Shi, Y. X.; Yang, M. Y.; Zhao, W.; Sun, Z. H.;Weng, J. Q.; Tan, C. X.; Liu, X. H.; Li, B. J.; Zhang, Y. G. Lett. Drug Des. Discovery 2016, 13, 521.
[15] Liu, X. H.; Tan, C. X.; Weng, J. Q. Phosphorus, Sulfur Silicon Relat. Elem. 2011, 186, 552.
[16] Zhang, L. J.; Yang, M. Y.; Sun, Z. H.; Tan, C. X.; Weng, J. Q.; Wu, H. K.; Liu, X. H. Lett. Drug Des. Discovery 2014, 11, 1107.
[17] Liu, X. H.; Fang, Y. M.; Xie, F.; Zhang, R. R.; Shen, Z. H.; Tan, C. X.; Weng, J. Q.; Xu, T. M.; Huang, H. Y. Pest Manage. Sci. 2017, DOI:10.1002/ps.4556.
[18] Yan, S. L.; Yang, M. Y.; Sun, Z. H.; Min, L. J.; Tan, C. X.; Weng, J. Q.; Wu, H. K.; Liu, X. H. Lett. Drug Des. Discovery 2014, 11, 940.
[19] Zhao, W.; Shen, Z. H.; Xing, J. H.; Yang, G.; Xu, T. M.; Peng, W. L.; Liu, X. H. Chem. Pap. 2017, 71, 921.
[20] Zhao, W.; Shen, Z. H.; Xing, J. H.; Xu, T. M.; Peng, W. L.; Liu, X. H. Chin. J. Struct. Chem. 2017, 36, 423.
[21] Zhao, W.; Shen, Z. H.; Xu, T. M.; Peng, W. L.; Liu, X.-H. J. Heterocycl. Chem. 2017, 54, 1751.
[22] Liu, X. H.; Zhao, W.; Shen, Z. H.; Xing, J. H.; Xu, T. M.; Peng, W. L. Eur. J. Med. Chem. 2017, 125, 881.
[23] Zhao, W.; Shen, Z. H.; Xu, T. M.; Peng, W. L.; Liu, X. H. Lett. Drug Des. Discovery 2017, 14, 323.
[24] Shen, Z. H.; Shi, Y. X.; Yang, M. Y.; Sun, Z. H.; Weng, J. Q.; Tan, C. X.; Liu, X. H.; Li, B. J.; Zhao, W. G. Chin. J. Struct. Chem.2016, 35, 457.
[25] Vasilevskii, S. F.; Shvartsberg, M. S. Bull. Acad. Sci. USSR, Chem. Sci. 1990, 39, 1901.
[26] Liu, X. H.; Tan, C. X.; Weng, J. Q. Phosphorus, Sulfur Silicon Relat. Elem. 2011, 186, 558.
[27] Zhai, Z. W.; Wang, Q.; Shen, Z. H.; Tan, C. X.; Weng, J. Q.; Liu, X. H. Chin. J. Org. Chem. 2017, 37, 232(in Chinese). (翟志文, 汪乔, 沈钟华, 谭成侠, 翁建全, 刘幸海, 有机化学, 2017, 37, 232.)

Options
Outlines

/

〈 〉