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Synthesis and biological activity of novel 1-substituted phenyl(glycosyl)-4-{4-[4,6-dimethoxy)pyrimidin-2-yl] piperazin-1-yl}methyl-1H-1,2,3-triazoles

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Chemical Research in Chinese Universities Aims and scope

Abstract

A series of novel 1-substituted phenyl or glycosyl 1,2,3-triazoles was designed and synthesized by azide-alkyne 1,3-dipolar cycloaddition between 4,6-dimethoxy-2-[4-prop-2-ynyl)piperazin-1-yl] pyrimidine and each of different azides catalysed by in situ generated Cu(I). The O-acyl protecting groups on glycosyl 1,2,3-triazoles were removed by triethylamine in wet methanol. Their chemical structures were established on the basis of corresponding 1H NMR, 13C NMR, MS and elemental analysis. The fungicidal activities of target compounds were evaluated in vitro against Fusarium omysporum, Physalospora piricola, Alternaria solani, Phytophthora capsici, Cercospora arachidicola and Gibberella zeae at 50 μg/mL. The bioassay results indicate that some of the compounds exhibited moderate but promising fungicidal activities. In particular, acetylated glucopyranosyl triazole displayed a good fungicidal activity against Physalospora piricola, which is equal to that of the positive control compound chlorothalonil.

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References

  1. Sharma P., Kumar A., Upadhyay S., Singh J., Sahu V., Med. Chem. Res., 2010, 19, 589

    Article  CAS  Google Scholar 

  2. Zhao X., Lu J. R., Xin C. W., Lu B. W., Bao X. R., Li J. F., Liu Y., Yang X. Y., Yuan Y., Chem. Res. Chinese Universities, 2012, 28(3), 424

    CAS  Google Scholar 

  3. Jordao A. K., Afonso P. P., Ferreira V. F., Maria C. B. V., Souza M. C. B. V., Maria C. B., Almeida M. C. B., Beltrame C. O., Paiva D. P., Wardell S. M. S. V., Wardell J. L., Tiekink E. R. T., Damaso C. R., Cunha A. C., Eur. J. Med. Chem., 2009, 44, 3777

    Article  CAS  Google Scholar 

  4. Genin M. J., Allwine D. A., Anderson D. J., Barbachyn M. R., Emmert D. E., Garmon S. A., Graber D. R., Grega K. C., Hester J. B., Hutchinson D. K., Morris J., Reischer R. J., Ford C. W., Zurenko G. E., Hamel J. C., Schaadt R. D., Stapert D., Yagi B. H., J. Med. Chem., 2000, 43, 953

    Article  CAS  Google Scholar 

  5. Al-Masoudi N. A., Al-Soud Y. A., Tetrahedron Lett., 2002, 43, 4021

    Article  CAS  Google Scholar 

  6. Hager C., Miethchen R., Reinke H., J. Fluor. Chem., 2000, 104, 135

    Article  CAS  Google Scholar 

  7. Huisgen R.; Ed.: Padwa A., 1,3-Dipolar Cycloaddition Chemistry, Wiley, New York, 1984, 1

  8. Tripathi R. P., Yadav A. K., Ajay A., Bisht S. S., Chaturvedi V., Sinha S. K., Eur. J. Med. Chem., 2010, 45, 142

    Article  CAS  Google Scholar 

  9. Salehi P., Dabiri M., Koohshari M., Movahed S. K., Bararjanian M., Mol. Divers., 2011, 15, 833

    Article  CAS  Google Scholar 

  10. Rostovtsev V. V., Green L. G., Fokin V. V., Sharpless K. B., Angew. Chem. Int. Ed., 2002, 41, 2596

    Article  CAS  Google Scholar 

  11. Walter M., Kottke T., Weizel L., Schwed J. S., Stark H., Synthesis, 2011, 17, 2733

    Google Scholar 

  12. Awad O. M. E., Attia W. E., El Ashry E. S. H., Carbohydr. Res., 2004, 339, 469

    Article  Google Scholar 

  13. Wang H. A., Li Y. X., Li Z. M., Cheng H. Y., Wang S. H., Liu B., Chem. Res. Chinese Universities, 2009, 25(1), 52

    Google Scholar 

  14. Wang W., Li X. L., Li R., Zhang P. Z., Chen H., Chem. J. Chinese Universities, 2012, 33(5), 958

    CAS  Google Scholar 

  15. El-Sayed H. A., Moustafa A. H., Haikal A. E. F. Z., Abu-El-Halawa R., El Ashry E. S. H., Eur. J. Med. Chem., 2011, 46, 2948

    Article  CAS  Google Scholar 

  16. Zhang J. J., Garrossian M., Gardner D., Garrossian A., Chang Y. T., Kim Y. K., Chang C. W. T., Bioorg. Med. Chem. Lett., 2008, 18, 1359

    Article  CAS  Google Scholar 

  17. Rossi L. L., Basu A., Bioorg. Med. Chem. Lett., 2005, 15, 3596

    Article  CAS  Google Scholar 

  18. De Las Heras F. G., Alonso R., Alonso G., J. Med. Chem., 1979, 22, 496

    Article  Google Scholar 

  19. Wang M. Z., Xu H., Feng Q., Wang L. Z., Wang S. H., Li, Z. M., J. Agric. Food. Chem., 2009, 57, 7912

    Article  CAS  Google Scholar 

  20. Wang B. L., Shi Y. X., Ma Y., Liu X. H., Li Y. H., Song H. B., Li B. J., Li Z. M., J. Agric. Food. Chem., 2010, 58, 5515

    Article  CAS  Google Scholar 

  21. Chaudhary P., Kumar R., Verma A. K., Singh D., Yadav V., Chhillar A. K., Sharmab G. L., Chandra R., Bioorg. Med. Chem., 2006, 14, 1819

    Article  CAS  Google Scholar 

  22. Upadhayaya R. S., Sinha N., Jain S., Kishore N., Chandra R., Arora S. K., Bioorg. Med. Chem., 2004, 12, 2225

    Article  CAS  Google Scholar 

  23. Von Moltke L. L., Greenblatt D. J., Grassi J. M., Granda B. W., Fogelman S. M., Harmatz J. S., Kramer S. J., Fabre L. F., Shader R. I., Psychopharmacology, 1998, 140, 293

    Article  Google Scholar 

  24. Kossakowski J., Pakosinska-Parys M., Struga M., Dybala I., Koziol A. E., La Colla P., Ester Marongiu L., Ibba C., Collu D., Loddo R., Molecules, 2009, 14, 5189

    Article  CAS  Google Scholar 

  25. Mao M. Z., Li Y. X., Zhou Y. Y., Chen W., Liu T. W., Yu S. J., Wang S. H., Li Z. M., Chem. Biol. Drug. Des., 2011, 78, 695

    Article  CAS  Google Scholar 

  26. Acquaah-Harrison G., Zhou S., Hines J. V., Bergmeier S. C., J. Comb. Chem., 2010, 12, 491

    Article  CAS  Google Scholar 

  27. Bunnelle W. H., J. Org. Chem., 2011, 76, 5429

    Article  CAS  Google Scholar 

  28. Chen N. C., Bioassay of Pesticides, Beijing Agricultural University Press, Beijing, 1991, 161

    Google Scholar 

  29. Hu M. Y., Li J. Q., Yao S. Q., Org. Lett., 2008, 10, 5529

    Article  CAS  Google Scholar 

  30. Tropper F. D., Andersson F. O., Braun S., Roy R., Synthesis, 1992, 7, 618

    Article  Google Scholar 

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Author notes

  1. Xiao-ping Yang

    Present address: Division of Medical Oncology, Department of Medicine, School of Medicine, University of Colorado Denver, Aurora, CO, 80045, USA

Authors and Affiliations

  1. State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, P. R. China

    Ming-zhen Mao, Yu-xin Li, Yun-yun Zhou, Xiu-lan Zhang, Xiao Zhang & Zheng-ming Li

  2. School of Pharmacy, University of Wyoming, Laramie, WY, 82071, USA

    Xiao-ping Yang

Authors
  1. Ming-zhen Mao
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  2. Yu-xin Li
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  3. Yun-yun Zhou
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  4. Xiao-ping Yang
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  5. Xiu-lan Zhang
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Corresponding authors

Correspondence to Yu-xin Li or Zheng-ming Li.

Additional information

Supported by the National Basic Research Program of China(No.2010CB126106), the Fundamental Research Funds for the Central Universities and Natural Science Foundation of China(No.31000861).

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Mao, Mz., Li, Yx., Zhou, Yy. et al. Synthesis and biological activity of novel 1-substituted phenyl(glycosyl)-4-{4-[4,6-dimethoxy)pyrimidin-2-yl] piperazin-1-yl}methyl-1H-1,2,3-triazoles. Chem. Res. Chin. Univ. 29, 900–905 (2013). https://doi.org/10.1007/s40242-013-2338-x

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  • DOI: https://doi.org/10.1007/s40242-013-2338-x

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