Novel Schiff bases derived from isothiocyanates: synthesis, characterization, and antioxidant activity

Abstract

A series of novel thiosemicarbazones including Schiff bases were synthesized by treatment of various aryl-substituted aldehydes with thiosemicarbazides in ethanol containing one drop of hydrochloric acid at reflux for 3–5 h. For this, thiosemicarbazides were obtained from hydrazine monohydrate and isothiocyanates in cold dry ethanol at 0 °C for 1 h. FT-IR, 1H NMR, 13C NMR, and LC–MS/MS spectroscopic methods and elemental analysis were used to characterize the identification of the synthesized products. The in vitro antioxidant activity of these compounds was tested by the 1,1-diphenyl-2-picryl hydrazyl (DPPH) free radical trapping method. All of the synthesized compounds showed lower antioxidant activity than the ascorbic acid standard and followed the sequence I > VII > X > VI > IV > IX > XI > II > V > III > VIII.

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References

  1. 1.

    A. Goszczyńska, H. Kwiecień, K. Fijałkowski. Med. Chem. Res. 24, 3561 (2015)

    Article  Google Scholar 

  2. 2.

    A. Cinarli, D. Gürbüz, A. Tavman, A.S. Birteksöz. Bull. Chem. Soc. Ethiop. 25, 407 (2011)

    CAS  Article  Google Scholar 

  3. 3.

    A. Jarrahpour, D. Khalili, E. De Clercq, C. Salmi, J. Brunel, Molecules 12, 1720 (2007)

    CAS  Article  Google Scholar 

  4. 4.

    S. Bharti, G. Nath, R. Tilak, S. Singh, Eur. J. Med. Chem. 45, 651 (2010)

    CAS  Article  Google Scholar 

  5. 5.

    T.K. Bakır, J.B. Lawag, Res. Chem. Intermed. 46, 2541 (2020)

    Article  Google Scholar 

  6. 6.

    Y. Zhang, Y. Fang, H. Liang, H. Wang, K. Hu, X. Liu, X. Yi, Y. Peng, Bioorg. Med. Chem. Lett. 23, 107 (2013)

    Article  Google Scholar 

  7. 7.

    K.S. Kumar, S. Ganguly, R. Veerasamy, E. De Clercq, Eur. J. Med. Chem. 45, 5474 (2010)

    CAS  Article  Google Scholar 

  8. 8.

    S. Pandeya, D. Sriram, G. Nath, E. De Clercq, Pharm. Acta Helv. 74, 11 (1999)

    CAS  Article  Google Scholar 

  9. 9.

    M.J. Hearn, M.H. Cynamon, M.F. Chen, R. Coppins, J. Davis, H.J.-O. Kang, A. Noble, B. Tu-Sekine, M.S. Terrot, D. Trombino, Eur. J. Med. Chem. 44, 4169 (2009)

    CAS  Article  Google Scholar 

  10. 10.

    S.M. Emam, I.E. El Sayed, M.I. Ayad, H.M. Hathout, J. Mol. Struct. 1146, 600 (2017)

    CAS  Article  Google Scholar 

  11. 11.

    B. Mohan Sahoo, S. Chandra Dinda, B.V. Ravi Kumar, J. Panda, P.S. Brahmkshatriya, Lett. Drug Des. Discov. 11, 82 (2014)

    Article  Google Scholar 

  12. 12.

    S.K. Sridhar, S.N. Pandeya, J.P. Stables, A. Ramesh, Eur. J. Pharm. Sci. 16, 129 (2002)

    CAS  Article  Google Scholar 

  13. 13.

    M.M. Aly, Y.A. Mohamed, K.A. El-Bayouki, W.M. Basyouni, S.Y. Abbas, Eur. J. Med. Chem. 45, 3365 (2010)

    CAS  Article  Google Scholar 

  14. 14.

    H. Pervez, M.S. Iqbal, M.Y. Tahir, F.H. Nasim, M.I. Choudhary, K.M. Khan, J. Enzyme Inhib. Med. Chem. 23, 848 (2008)

    CAS  Article  Google Scholar 

  15. 15.

    H. Govender, C. Mocktar, H.M. Kumalo, N.A. Koorbanally, Phosphorus Sulfur Relat. Elem. 194, 1074 (2019)

    CAS  Article  Google Scholar 

  16. 16.

    S. Ghosh, A.K. Misra, G. Bhatia, M. Khan, A. Khanna, Bioorg. Med. Chem. Lett. 19, 386 (2009)

    CAS  Article  Google Scholar 

  17. 17.

    M. Bingul, E. Şenkuytu, M.F. Saglam, M. Boga, H. Kandemir, I.F. Sengul, Res. Chem. Intermed. 45, 4487 (2019)

    CAS  Article  Google Scholar 

  18. 18.

    H. Muğlu, Res. Chem. Intermed. 46, 2083 (2020)

    Article  Google Scholar 

  19. 19.

    T.R. Bal, B. Anand, P. Yogeeswari, D. Sriram, Bioorg. Med. Chem. Lett. 15, 4451 (2005)

    CAS  Article  Google Scholar 

  20. 20.

    A. Kshirsagar, M.P. Toraskar, V.M. Kulkarni, S. Dhanashire, V. Kadam. Int. J. Chem. Tech. Res 1, 696 (2009)

    CAS  Google Scholar 

  21. 21.

    C. Shipman Jr., S.H. Smith, J.C. Drach, D.L. Klayman, Antimicrob. Agents Chemother. 19, 682 (1981)

    CAS  Article  Google Scholar 

  22. 22.

    N. Solak, S. Rollas, Arkivoc xii, 173 (2006)

    Google Scholar 

  23. 23.

    W. Hu, W. Zhou, C. Xia, X. Wen, Bioorg. Med. Chem. Lett. 16, 2213 (2006)

    CAS  Article  Google Scholar 

  24. 24.

    H. Pervez, N. Manzoor, M. Yaqub, A. Khan, K.M. Khan, F-u-H Nasim, M.I. Choudhary, Lett. Drug Des. Discov. 7, 102 (2010)

    CAS  Article  Google Scholar 

  25. 25.

    B. Halliwell, J.M. Gutteridge, Free radicals in biology and medicine (Oxford University Press, Oxford, 2015)

    Google Scholar 

  26. 26.

    Y.K. Tyagi, A. Kumar, H.G. Raj, P. Vohra, G. Gupta, R. Kumari, P. Kumar, R.K. Gupta, Eur. J. Med. Chem. 40, 413 (2005)

    CAS  Article  Google Scholar 

  27. 27.

    W. Brand-Williams, M.-E. Cuvelier, C. Berset, LWT-Food. Sci. Technol. 28, 25 (1995)

    CAS  Google Scholar 

  28. 28.

    N. Naik, H.V. Kumar, P.B. Vidyashree, J. Pharm. Res. 4, 2686 (2011)

    CAS  Google Scholar 

  29. 29.

    E.N. Frankel, A.S. Meyer, J. Sci. Food Agric. 80, 1925 (2000)

    CAS  Article  Google Scholar 

  30. 30.

    K.H.D. Reddy, S.-M. Lee, K. Seshaiah, R.K. Babu, J. Serb. Chem. Soc. 78, 229 (2013)

    CAS  Article  Google Scholar 

  31. 31.

    P. Tarasconi, S. Capacchi, G. Pelosi, M. Cornia, R. Albertini, A. Bonati, P.P. Dall'Aglio, P. Lunghi, S. Pinelli, Bioorg. Med. Chem. 8, 157 (2000)

    CAS  Article  Google Scholar 

  32. 32.

    D. Williams, I. Fleming, Spectroscopic methods in organic chemistry (McGraw Hill Book Co. Ltd, Maidenhead, 1973)

    Google Scholar 

  33. 33.

    C. Hansch, A. Leo, R. Taft, Chem. Rev. 91, 165 (1991)

    CAS  Article  Google Scholar 

  34. 34.

    H. Muğlu, M.S. Çavuş, T. Bakır, H. Yakan, J. Mol. Struct. 1196, 819 (2019)

    Article  Google Scholar 

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Acknowledgements

I would like to thank the Scientific Technological Research and Applications Center (Gübitam) and Dr. Ömer Faruk Ensari for taking the NMR spectra.

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Correspondence to Hasan Yakan.

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Yakan, H. Novel Schiff bases derived from isothiocyanates: synthesis, characterization, and antioxidant activity. Res Chem Intermed 46, 3979–3995 (2020). https://doi.org/10.1007/s11164-020-04185-w

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Keywords

  • Schiff bases
  • Isothiocyanates
  • Thiosemicarbohydrazides
  • Antioxidant activity
  • Spectroscopic elucidation