Abstract
A series of some new 1,2-bis-(4-amino-5-mercapto-1,2,4-triazol-3-yl)-ethane derivatives 3–18 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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N. Demirbas, D.A. Ugurluoglu, Bioorg. Med. Chem. 3717, 10 (2002)
S. Kiran, B.M. Singh, T. Parikshit, Eur. J. Med. Chem. 147, 41 (2006)
L.G. Almajan, I. Saramet, S.F. Barbuceanu, C. Draghici, G. Bancescu, Rev. Chem. (Bucharest) 896, 60 (2009)
J. Wu, X. Liu, X. Cheng, Y. Cao, D. Wang, Z. Li, W. Xu, C. Pannecouque, M. Witvrouw, E. Declereq, Molecules 2003, 12 (2007)
B.S. Holla, B. Veerendra, M.K. Shivananda, B. Poojary, Eur. J. Med. Chem. 759, 38 (2003)
S. Jubie, P. Sikdar, S. Antony, R. Kalirajan, B. Gowramma, S. Gomathy, K. Elango, Pak. J. Pharm. Sci. 109, 24 (2011)
A.R. Prasad, T. Ramalingam, A.B. Rao, P.W. Diwan, P.B. Sattur, Eur. J. Med. Chem. 199, 24 (1989)
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)
S.F. Barbuceanu, G. Saramet, G.L. Almajan, C. Draghici, F. Barbuceanu, G. Bancescu, Bioorg. Med. Chem. 417, 49 (2012)
R. Sharma, G.P. Misra, J. Sainy, S.C. Chaturvedi, Med. Chem. Res. 245, 20 (2011)
B.W. Dymock, P.S. Jones, F.X. Wilson, Antivir. Chemother. 79, 11 (2000)
A.H. Moustafa, R.A. Haggam, M.E. Younes, E.S.H. El Ashry, Nucleosides, Nucleotides Nucleic Acids 1885, 24 (2005)
A.H. Moustafa, R.A. Haggam, M.E. Younes, E.S.H. El Ashry, Phosphorus Sulfur Silicon 2361, 181 (2006)
R.A. Haggam, Res. Chem. Intermed. 1135, 41 (2015)
R.A. Haggam, J. Conrad, U. Beifuss, Tetrahedron Lett. 6627, 50 (2009)
R.A. Haggam, Tetrahedron 6488, 69 (2013)
R.A. Haggam, Res. Chem. Intermed. 8195, 41 (2015)
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
J.P. Tierney, P. Lidstrom, Microwave Assisted Organic Synthesis (Blackwell, Oxford, 2005)
C.O. Kappe, Angew. Chem. Int. Ed. 6250, 43 (2004)
C.O. Kappe, Angew. Chem. Int. Ed. 6408, 116 (2004)
E.S.H. El Ashry, L.F. Awad, H. Abdelhamid, A.I. Atta, Nucleosides. Nucleotides Nucleic Acids 325, 25 (2006)
A.L. Barry, Procedures Antibiotics in Laboratory Medicine (Lorin Williams Wilkians Co., Baltimore, 1980)
M.M. Ghorab, AMSh El-Sharief, Y.A. Ammar, ShI Mohamed, II Farmaco 354, 55 (2000)
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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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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DOI: https://doi.org/10.1007/s11164-016-2538-3