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Synthesis and cyclization of some 1,2-bis-(4-amino-5-mercapto-1,2,4-triazol-3-yl)-ethane derivatives under conventional and microwave conditions: antimicrobial activity

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Abstract

A series of some new 1,2-bis-(4-amino-5-mercapto-1,2,4-triazol-3-yl)-ethane derivatives 318 were designed and synthesized from succinic acid via conventional heating and microwave (MW) irradiation. A benign synthesis was planned so as to take the advantages of Microwave Assisted Organic Synthesis technique. Better yields and shorter reaction times were realized using MW. The structures of the prepared compounds have been elucidated unambiguously by FT-IR, 1H/13C Nuclear Magnetic Resonance (NMR)-spectroscopic methods including HH-Correlation Spectroscopy (COSY), Heteronuclear Single Quantum Spectroscopy (HSQC) and Heteronuclear Multiple-Bond Spectroscopy (HMBC) experiments. Results of the minimal inhibitory concentration for some selected compounds exhibited potential activity against both bacteria and fungi, comparing with the standard drugs Cefotaxime and Nystatin.

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References

  1. N. Demirbas, D.A. Ugurluoglu, Bioorg. Med. Chem. 3717, 10 (2002)

    Google Scholar 

  2. S. Kiran, B.M. Singh, T. Parikshit, Eur. J. Med. Chem. 147, 41 (2006)

    Google Scholar 

  3. L.G. Almajan, I. Saramet, S.F. Barbuceanu, C. Draghici, G. Bancescu, Rev. Chem. (Bucharest) 896, 60 (2009)

    Google Scholar 

  4. J. Wu, X. Liu, X. Cheng, Y. Cao, D. Wang, Z. Li, W. Xu, C. Pannecouque, M. Witvrouw, E. Declereq, Molecules 2003, 12 (2007)

    Google Scholar 

  5. B.S. Holla, B. Veerendra, M.K. Shivananda, B. Poojary, Eur. J. Med. Chem. 759, 38 (2003)

    Google Scholar 

  6. S. Jubie, P. Sikdar, S. Antony, R. Kalirajan, B. Gowramma, S. Gomathy, K. Elango, Pak. J. Pharm. Sci. 109, 24 (2011)

    Google Scholar 

  7. A.R. Prasad, T. Ramalingam, A.B. Rao, P.W. Diwan, P.B. Sattur, Eur. J. Med. Chem. 199, 24 (1989)

    Google Scholar 

  8. I. Khan, S. Ali, S. Hameed, N.H. Rama, M.T. Hussain, A. Wadood, R. Uddin, Z. Ul-Haq, A. Khan, M.I. Choudhary, Eur. J. Med. Chem. 5200, 45 (2010)

    Google Scholar 

  9. S.F. Barbuceanu, G. Saramet, G.L. Almajan, C. Draghici, F. Barbuceanu, G. Bancescu, Bioorg. Med. Chem. 417, 49 (2012)

    Google Scholar 

  10. R. Sharma, G.P. Misra, J. Sainy, S.C. Chaturvedi, Med. Chem. Res. 245, 20 (2011)

    Google Scholar 

  11. B.W. Dymock, P.S. Jones, F.X. Wilson, Antivir. Chemother. 79, 11 (2000)

    Google Scholar 

  12. A.H. Moustafa, R.A. Haggam, M.E. Younes, E.S.H. El Ashry, Nucleosides, Nucleotides Nucleic Acids 1885, 24 (2005)

    Google Scholar 

  13. A.H. Moustafa, R.A. Haggam, M.E. Younes, E.S.H. El Ashry, Phosphorus Sulfur Silicon 2361, 181 (2006)

    Google Scholar 

  14. R.A. Haggam, Res. Chem. Intermed. 1135, 41 (2015)

    Google Scholar 

  15. R.A. Haggam, J. Conrad, U. Beifuss, Tetrahedron Lett. 6627, 50 (2009)

    Google Scholar 

  16. R.A. Haggam, Tetrahedron 6488, 69 (2013)

    Google Scholar 

  17. R.A. Haggam, Res. Chem. Intermed. 8195, 41 (2015)

    Google Scholar 

  18. J. Hamelin, J.P. Bazureau, F. Texier-Boullet, in Microwave in Organic Synthesis, vol. 253, ed. by A. Loupy (Wiley-VCH, New York, 2002), p. 253

    Google Scholar 

  19. J.P. Tierney, P. Lidstrom, Microwave Assisted Organic Synthesis (Blackwell, Oxford, 2005)

    Book  Google Scholar 

  20. C.O. Kappe, Angew. Chem. Int. Ed. 6250, 43 (2004)

    Google Scholar 

  21. C.O. Kappe, Angew. Chem. Int. Ed. 6408, 116 (2004)

    Google Scholar 

  22. E.S.H. El Ashry, L.F. Awad, H. Abdelhamid, A.I. Atta, Nucleosides. Nucleotides Nucleic Acids 325, 25 (2006)

    Google Scholar 

  23. A.L. Barry, Procedures Antibiotics in Laboratory Medicine (Lorin Williams Wilkians Co., Baltimore, 1980)

    Google Scholar 

  24. M.M. Ghorab, AMSh El-Sharief, Y.A. Ammar, ShI Mohamed, II Farmaco 354, 55 (2000)

    Google Scholar 

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Acknowledgments

The author is very grateful to Hohenheim University, Institute of Biorganic Chemistry, Stuttgart, for providing the research facilities to perform the analyses and correlations spectra presented in this article. I would also like to thank Dr. Ashraf Sabry, assistant professor of microbiology, Zagazig University, Faculty of Science for carrying out the biological section.

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Correspondence to Reda A. Haggam.

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Haggam, R.A. Synthesis and cyclization of some 1,2-bis-(4-amino-5-mercapto-1,2,4-triazol-3-yl)-ethane derivatives under conventional and microwave conditions: antimicrobial activity. Res Chem Intermed 42, 7313–7328 (2016). https://doi.org/10.1007/s11164-016-2538-3

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