Skip to main content

Advertisement

SpringerLink
Log in

A green one-pot synthesis of 3(5)-substituted 1,2,4-triazol-5(3)-amines as potential antimicrobial agents

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

An efficient procedure was proposed for the synthesis of 3(5)-substituted 1,2,4-triazol-5(3)-amines via a one-pot reaction of thiourea, dimethyl sulfate and various hydrazides. 1,2,4-Triazole derivatives were prepared in aqueous media under mild conditions while adhering to some principles of green chemistry. The products were easily isolated in 83–95% yields without any need for further purification. Inhibitory activities of all synthetic compounds were assessed against a variety of Gram-positive and Gram-negative pathogenic bacteria as well as some fungal pathogens. The best antibacterial effects were observed with 3(5)-phenyl-1H-1,2,4-triazol-5(3)-amine according to its MIC values (4–8 μg mL−1). All compounds were successful in blocking the growth of fungi. Acceptable antioxidant properties were observed only with 3(5)-(4-nitrophenyl)-1H-1,2,4-triazol-5(3)-amine.

Graphic abstract

3(5)-Substituted 1,2,4-triazol-5(3)-amines were efficiently prepared via a one-pot reaction of thiourea, dimethyl sulfate and various hydrazides in water as the solvent. Inhibitory activity of all synthesized derivatives was proved according to their MIC, MBC and MFC values. It is found that they are potential antifungal agents.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Scheme 2
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. R.P. Myers, H. Shah, K.W. Burak, C. Cooper, J.J. Feld, Can. J. Gastroenterol. Hepatol. 29, 19 (2015)

    PubMed  PubMed Central  Google Scholar 

  2. J. Riss, J. Cloyd, J. Gates, S. Collins, Acta Neurol. Scand. 118, 69 (2008)

    CAS  PubMed  Google Scholar 

  3. O. Garcia-Algar, M.A. Lopez-Vilchez, I. Martin, A. Mur, M. Pellegrini, R. Pacifici, S. Rossi, S. Pichini, Clin. Toxicol. (Phila) 45, 295 (2007)

    CAS  Google Scholar 

  4. WHO expert committee on drug dependence: thirty-ninth report. World Health Organization–Technical Report Series,1009, 1–20, 2017

  5. K. Wellington, G.L. Plosker, Drugs 62, 1539 (2002)

    CAS  PubMed  Google Scholar 

  6. S. Liu, Y. Hou, X. Chen, Y. Gao, H. Li, S. Sun, Int. J. Antimicrob. Agents 43, 395 (2014)

    CAS  PubMed  Google Scholar 

  7. T. Patel, S. Dhillon, Drugs 73, 1977 (2013)

    CAS  PubMed  Google Scholar 

  8. C. Ju, J. Xu, X. Wu, F. Dong, X. Liu, C. Tian, Y. Zheng, Sci. Total Environ. 609, 655 (2017)

    CAS  PubMed  Google Scholar 

  9. Z. Kong, M. Li, J. An, J. Chen, Y. Bao, F. Francis, X. Dai, Sci. Rep. 6, 33552 (2016)

    CAS  PubMed  PubMed Central  Google Scholar 

  10. M.J.E. Roelofs, A.R. Temming, A.H. Piersma, M. van den Berg, M.B.M. van Duursen, Toxicol. Rep. 1, 271 (2014)

    CAS  PubMed  PubMed Central  Google Scholar 

  11. J. Pernak, B. Markiewicz, B. Łęgosz, F. Walkiewicz, F. Gwiazdowski, T. Praczyk, RSC Adv. 5, 9695 (2015)

    CAS  Google Scholar 

  12. Y.A. Al-Soud, N.A. Al-Masoudi, A.E.S. Ferwanah, Bioorg. Med. Chem. 11, 1701 (2003)

    CAS  PubMed  Google Scholar 

  13. R. Singh, S.K. Kashaw, V.K. Mishra, M. Mishra, V. Rajoriya, V. Kashaw, Indian J. Pharm. Sci. 80, 36 (2018)

    Google Scholar 

  14. N. Upmanyu, J.K. Gupta, K. Shah, P. Mishra, Pharm. Chem. J. 45, 433 (2011)

    CAS  Google Scholar 

  15. M.V. Papadopoulou, W.D. Bloomer, H.S. Rosenzweig, E. Chatelain, M. Kaiser, S.R. Wilkinson, C. McKenzie, J.R. Ioset, J. Med. Chem. 55, 5554 (2012)

    CAS  PubMed  PubMed Central  Google Scholar 

  16. K. Karrouchi, L. Chemlal, J. Taoufik, Y. Cherrah, S. Radi, M. El Abbes Faouzi, M. Ansar, Ann. Pharm. Fr. 74, 431 (2016)

    CAS  PubMed  Google Scholar 

  17. G.M. Shelke, V.K. Rao, M. Jha, T.S. Cameron, A. Kumar, Synlett 26, 404 (2015)

    CAS  Google Scholar 

  18. S. Ueda, H. Nagasawa, J. Am. Chem. Soc. 131, 15080 (2009)

    CAS  PubMed  Google Scholar 

  19. H. Huang, W. Guo, W. Wu, C.J. Li, H. Jiang, Org. Lett. 17, 2894 (2015)

    CAS  PubMed  Google Scholar 

  20. Z. Chen, H. Li, W. Dong, M. Miao, H. Ren, Org. Lett. 18, 1334 (2016)

    CAS  PubMed  Google Scholar 

  21. A. Gogoi, S. Guin, S. Rajamanickam, S.K. Rout, B.K. Patel, J. Org. Chem. 80, 9016 (2015)

    CAS  PubMed  Google Scholar 

  22. L.Y. Wang, W.C. Tseng, H.Y. Lin, F.F. Wong, Synlett 2011, 1467 (2011)

    Google Scholar 

  23. Y. Xu, M. McLaughlin, E.N. Bolton, R.A. Reamer, J. Org. Chem. 75, 8666 (2010)

    CAS  PubMed  Google Scholar 

  24. B. Wong, A. Stumpf, D. Carrera, C. Gu, H. Zhang, Synthesis 45, 1083 (2013)

    CAS  Google Scholar 

  25. D.R. Godhani, A.A. Jogel, A.N. Sanghani, J.P. Mehta, Indian J. Chem. 54B, 556 (2015)

    CAS  Google Scholar 

  26. W.S. Bechara, I.S. Khazhieva, E. Rodriguez, A.B. Charette, Org. Lett. 17, 1184 (2015)

    CAS  PubMed  Google Scholar 

  27. D.V. Batchelor, D.M. Beal, T.B. Brown, D. Ellis, D.W. Gordon, P.S. Johnson, H.J. Mason, M.J. Ralph, T.J. Underwood, S. Wheeler, Synlett 2008, 2421 (2008)

    Google Scholar 

  28. S. Guin, S.K. Rout, N. Khatun, T. Ghosh, B.K. Patel, Tetrahedron 68, 5066 (2012)

    CAS  Google Scholar 

  29. R.C. Cioc, E. Ruijter, R.V.A. Orru, Green Chem. 16, 2958 (2014)

    CAS  Google Scholar 

  30. A. Tam, I.S. Armstrong, T.E. La Cruz, Org. Lett. 15, 3586 (2013)

    CAS  PubMed  Google Scholar 

  31. M. Aouali, D. Mhalla, F. Allouche, L. El Kaim, S. Tounsi, M. Trigui, F. Chabchoub, Med. Chem. Res. 24, 2732 (2015)

    CAS  Google Scholar 

  32. X. Jia, G. Xu, Z. Du, Y. Fu, Polyhedron 151, 515 (2018)

    CAS  Google Scholar 

  33. A. Padmaja, C. Rajasekhar, A. Muralikrishna, V. Padmavathi, Eur. J. Med. Chem. 46, 5034 (2011)

    CAS  PubMed  Google Scholar 

  34. M.O. Simon, C.J. Li, Chem. Soc. Rev. 41, 1415 (2012)

    CAS  PubMed  Google Scholar 

  35. P.R. Shildneck, W. Windus, Org. Syn. Coll. 2, 411 (1943)

    Google Scholar 

  36. M.O. Sydnes, Curr. Green Chem. 1, 216 (2014)

    CAS  Google Scholar 

  37. G.M. Castanedo, P.S. Seng, N. Blaquiere, S. Trapp, S.T. Staben, J. Org. Chem. 76, 1177 (2011)

    CAS  PubMed  Google Scholar 

  38. P. Yin, W.B. Ma, Y. Chen, W.C. Huang, Y. Deng, L. He, Org. Lett. 11, 5482 (2009)

    CAS  PubMed  Google Scholar 

  39. R. Mestres, Environ. Sci. Pollut. Res. Int. 12, 128 (2005)

    CAS  PubMed  Google Scholar 

  40. Z. Ye, M. Ding, Y. Wu, Y. Li, W. Huaa, F. Zhang, Green Chem. 20, 1732 (2018)

    CAS  Google Scholar 

  41. M. Nakka, R. Tadikonda, S. Rayavarapu, P. Sarakula, S. Vidavalur, Synthesis 47, 517 (2015)

    CAS  Google Scholar 

  42. P.T. Anastas, J.C. Warner, Green chemistry: theory and practice (Oxford University Press, New York, 1998), p. 30

    Google Scholar 

  43. M.D. Kakwani, N.H. Palsule Desai, A.C. Lele, M. Ray, M.G.R. Rajan, M.S. Degani, Bioorg. Med. Chem. Lett. 21, 6523 (2011)

    CAS  Google Scholar 

  44. E. Hoggarth, J. Chem. Soc. 0, 612 (1950)

    CAS  Google Scholar 

  45. Y. Huang, X.Q. Hu, D.P. Shen, Y.F. Chen, P.F. Xu, Mol. Divers 11, 73 (2007)

    CAS  PubMed  Google Scholar 

  46. M. Aghazadeh Tabrizi, P.G. Baraldi, E. Ruggiero, G. Saponaro, S. Baraldi, G. Poli, T. Tuccinardi, A. Ravani, F. Vincenzi, P.A. Borea, K. Varani, Eur. J. Med. Chem. 113, 11 (2016)

    CAS  PubMed  Google Scholar 

  47. A.V. Dolzhenko, G. Pastorin, A.V. Dolzhenko, W.K. Chui, Tetrahedron Lett. 50, 2124 (2009)

    CAS  Google Scholar 

  48. R.M. Claramunt, C. Lopez, M.D. Santa Maria, D. Sanz, J. Elguero, Prog. Nucl. Magn. Reson. Spectrosc. 49, 169 (2006)

    CAS  Google Scholar 

  49. A.V. Dolzhenko, A.V. Dolzhenko, W.K. Chui, Heterocycles 71, 429 (2007)

    CAS  Google Scholar 

  50. L.R. Peyton, S. Gallagher, M. Hashemzadeh, Drugs Today (Barc) 51, 705 (2015)

    CAS  Google Scholar 

  51. R. Romagnolia, F. Prencipe, P. Oliva, S. Baraldi, P.G. Baraldi, A. Brancale, S. Ferla, E. Hamel, R. Bortolozzi, G. Viola, Bioorg. Chem. 80, 361 (2018)

    Google Scholar 

  52. H. Bera, B.J. Tan, L. Sun, A.V. Dolzhenko, W.K. Chui, G.N.C. Chiu, Eur. J. Med. Chem. 67, 325 (2013)

    CAS  PubMed  Google Scholar 

  53. N. Huang, X. Qi, Y. Wang, Y. Sun, National Institute of Biological Sciences WO2017/152842, A1. (2017)

Download references

Acknowledgement

This study was funded by the University of Zabol (Grant Number UOZ-GR-9618-10).

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Zabol, Zabol, Iran

    Hamid Beyzaei, Zahra Khosravi & Reza Aryan

  2. Torbat Jam Faculty of Medical Sciences, Torbat Jam, Iran

    Behzad Ghasemi

Authors
  1. Hamid Beyzaei
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zahra Khosravi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Reza Aryan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Behzad Ghasemi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hamid Beyzaei.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Beyzaei, H., Khosravi, Z., Aryan, R. et al. A green one-pot synthesis of 3(5)-substituted 1,2,4-triazol-5(3)-amines as potential antimicrobial agents. J IRAN CHEM SOC 16, 2565–2573 (2019). https://doi.org/10.1007/s13738-019-01714-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-019-01714-2

Keywords

Search

Navigation