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Design, Synthesis and Biological Activities of Novel N-Aryl-1H-pyrazole-5-carboxylate Derivatives

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Chemical Research in Chinese Universities Aims and scope

Abstract

In an attempt to search for potent fungicide, a series of novel N-aryl-1H-pyrazole-5-carboxylate derivatives was designed and synthesized. Their chemical structures were characterized by 1H NMR spectra and high resolution mass spectrometry(HRMS). The preliminary bioassay results indicated that some target compounds displayed better fungicidal activities against certain fungi at 50 µg/mL or favorable antitumor activities at 5 µg/mL compared with chlorothalonil and 5-fluorouracil, respectively. The structure-activity relationship demonstrated that the introduction of ester group and amide bond was favorable to the improvement of activities against Physalospora piricola and Phytophthora capsici.

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References

  1. Mu J. X., Zhai Z. W., Tan C. X., Weng J. Q., Wu H. K., Duke S. O., Zhang Y. G., Liu X. H., J. Heterocyclic Chem., 2019, 56(3), 968

    Article  CAS  Google Scholar 

  2. Fu Y., Wang M. X., Zhang D., Hou Y. W., Gao S., Zhao L. X., Ye F., RSC Adv., 2017, 7(74), 46858

    Article  CAS  Google Scholar 

  3. Shi Y. J., Ye L. Y., Zhong S. L., Cao X. F., Dai H., Hong Y., Li C. J., Shi J., Wu J. M., Chin. J. Org. Chem., 2017, 37(7), 1844

    Article  CAS  Google Scholar 

  4. Shi J. J., Ren G. H., Wu N. J., Weng J. Q., Xu T. M., Liu X. H., Tan C. X., Chin. Chem. Lett., 2017, 28(8), 1727

    Article  CAS  Google Scholar 

  5. Lv X. H., Xiao J. J., Ren Z. L., Chu M. J., Wang P., Meng X. F., Li D. D., Cao H. Q., RSC Adv., 2015, 5(68), 55179

    Article  CAS  Google Scholar 

  6. Yao T. T., Xiao D. X., Li Z. S., Cheng J. L., Fang S. W., Du Y. J., Zhao J. H., Dong X. W., Zhu G. N., J. Agric. Food Chem., 2017, 65(26), 5397

    Article  CAS  Google Scholar 

  7. Shen Y., Li Z., Ma Q., Wang C. X., Chen X. Z., Miao Q., Han C., J. Agric. Food. Chem., 2016, 64(19), 3901

    Article  CAS  Google Scholar 

  8. Liu X. R., Wu H., He Z. Y., Ma Z. Q., Feng J. T., Zhan X., Molecules, 2014, 19(9), 14036

    Article  Google Scholar 

  9. Meng F. J., Sun T., Dong W. Z., Li M. H., Tuo Z. Z., Arch. Pharm.(Weinheim), 2016, 349(3), 168

    Article  CAS  Google Scholar 

  10. Jia H. Y., Bai F. X., Liu N., Liang X. H., Zhan P., Ma C. H., Jiang X. M., Liu X. Y., Eur. J. Med. Chem., 2016, 123, 202

    Article  CAS  Google Scholar 

  11. Wen J. C., Bao Y., Niu Q., Yang J. Y., Fan Y. B., Li J. H., Jing Y. K., Zhao L. X., Liu D., Eur. J. Med. Chem., 2016, 109, 350

    Article  CAS  Google Scholar 

  12. Liang X. W., Zang J., Zhu M. Y., Gao Q. W., Wang B. H., Xu W. F., Zhang Y. J., ACS Med. Chem. Lett., 2016, 7(10), 950

    Article  CAS  Google Scholar 

  13. Ibrahim H. S., Abou-Seri S. M., Tanc M., Elaasser M. M., Abdel-Aziz H. A., Supuran C. T., Eur. J. Med. Chem., 2015, 103, 583

    Article  CAS  Google Scholar 

  14. Yan T., Yu S. J., Liu P. F., Liu Z., Wang B. L., Xiong L. X., Li Z. M., Chin. J. Chem., 2012, 30(4), 919

    Article  CAS  Google Scholar 

  15. Lima L. M., Barreiro E. J., Curr. Med. Chem., 2005, 12(1), 23

    Article  CAS  Google Scholar 

  16. Xu J. Y., Dong W. L., Xiong L. X., Li Z. M., Chem. J. Chinese Universities, 2012, 33(2), 298

    Google Scholar 

  17. Zhang X. L., Li Y. X., Ma J. L., Zhu H. W., Wang B. L., Mao M. Z., Xiong L. X., Li Y. Q., Li Z. M., Bioorg. Med. Chem., 2014, 22(1), 186

    Article  Google Scholar 

  18. Zhang X. L., Liu A. L., Zhao Y., Xiong L. X., Li Z. M., Chem. Res. Chinese Universities, 2013, 29(6), 1134

    Article  CAS  Google Scholar 

  19. Zhou Z. L., Kher S. M., Cai S. X., Whittemore E. R., Espitia S. A., Hawkinson J. E., Tran M., Woodward R. M., Weber E., Keana J. F. W., Bioorg. Med. Chem., 2003, 11(8), 1769

    Article  CAS  Google Scholar 

  20. Chen N. C., Bioassay Technology for Pestcides, Beijing Agricultural University Press, Beijing, 1991, 161

    Google Scholar 

  21. Mosmann T., J. Immunol. Methods, 1983, 65(1/2), 55

    Article  CAS  Google Scholar 

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Correspondence to Xiulan Zhang or Zhengming Li.

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Supported by the Scientific Research Program of Tianjin Municipal Education Commission, China(No.2018KJ114).

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Zhang, X., Zhang, H., Ma, J. et al. Design, Synthesis and Biological Activities of Novel N-Aryl-1H-pyrazole-5-carboxylate Derivatives. Chem. Res. Chin. Univ. 36, 853–858 (2020). https://doi.org/10.1007/s40242-019-9274-3

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  • DOI: https://doi.org/10.1007/s40242-019-9274-3

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