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Synthesis and in vitro anticancer, antibacterial, and antioxidant studies of unsymmetrical Schiff base derivatives of 4-[(1E)-N-(2-aminoethyl)ethanimidoyl]benzene-1,3-diol

Abstract

Schiff bases such as 2-hydroxy-1-(4-hydroxyphenyl)ethanone (DHAP) and its derivatives have attracted attention because they are useful in design and development of novel organic compounds for potential pharmaceutical applications. In this work, a series of 4-[(1E)-N-(2-aminoethyl)ethanimidoyl]benzene-1,3-diol (4ah) Schiff bases were synthesized by reaction of ethylenediamine, DHAP, and appropriate aldehyde moieties. The compositions of the prepared compounds were established using elemental analysis and Fourier-transform infrared (FTIR) and ultraviolet–visible (UV–Vis) spectroscopies. The compounds were screened against three Gram-positive and three Gram-negative bacteria, and the results compared with standard drugs ciprofloxacin and amoxicillin. Compounds 4g, 4h were found to have higher activity against Staphylococcus aureus with minimum inhibitory concentration (MIC) value of 2.5 mg/mL, while compounds 4f and 4h inhibited Escherichia coli with MIC values of 2.5 and 5 mg/mL, respectively. The IC50 values of compounds 4ah for scavenging 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical ranged from 2.63 ± 0.79 to 3.85 ± 0.83 µM with good correlation coefficient of R 2 = 0.957–0.994. In vitro anticancer screening of the compounds showed that compounds 4f, 4h, and parthenolide efficiently affected cell viability of cancer cell line MCF-7 with IC50 values of 4.10 ± 1.32, 4.01 ± 2.26, and 0.44 ± 2.02 µM, respectively.

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References

  1. A. Kajal, S. Bala, S. Kamboj, N. Sharma, V. Saini, J. Catal. (2013). doi:10.1155/2013/893512

    Google Scholar 

  2. T.P. Yoon, E.N. Jacobsen, Science 299, 1691 (2003)

    Article  CAS  Google Scholar 

  3. P.G. Cozzi, Chem. Soc. Rev. 33, 410 (2004)

    Article  CAS  Google Scholar 

  4. H. Schiff, Justus Liebigs Annalen der Chemie 131, 118 (1864)

    Article  Google Scholar 

  5. I.P. Ejidike, P.A. Ajibade, Molecules 20, 9788 (2015)

    Article  CAS  Google Scholar 

  6. A.O. De Souza, F.C.S. Galetti, C.L. Silva, B. Bicalho, M.M. Parma, S.F. Fonseca, Quim. Nova 30, 1563 (2007)

    Google Scholar 

  7. Z. Guo, R. Xing, S. Liu, Z. Zhong, X. Ji, L. Wang, Carbohydr. Res. 342, 1329 (2007)

    Article  CAS  Google Scholar 

  8. I. Kostova, L. Saso, Curr. Med. Chem. 20, 4609 (2013)

    Article  CAS  Google Scholar 

  9. D.N. Dhar, C.L. Taploo, J. Sci. Ind. Res. 41, 501 (1982)

    CAS  Google Scholar 

  10. C.M. Da Silva, D.L. Da Silva, L.V. Modolo, R.B. Alves, M.A. De Resende, C.V.B. Martins, A. de Fatima, J. Adv. Res. 2, 1 (2011)

    Article  Google Scholar 

  11. P. Przybylski, A. Huczynski, K. Pyta, B. Brzezinski, F. Bartl, Curr. Org. Chem. 13, 124 (2009)

    Article  CAS  Google Scholar 

  12. B. Halliwell, J.M.C. Gutteridge, Free Radicals in Biology and Medicine, 3rd edn. (Oxford University Press, New York, 1999)

    Google Scholar 

  13. P. Arulpriya, P. Lalitha, S. Hemalatha, Merr Der Chemica Sinica 1, 73 (2010)

    CAS  Google Scholar 

  14. G. Poli, G. Leonarduzzi, F. Biasi, E. Chiarpotto, Curr. Med. Chem. 11, 1163 (2004)

    Article  CAS  Google Scholar 

  15. A.K. Saxena, P. Raj, S.K. Dixit, Synth. React. Inorg. Met. Org. Chem. 20, 199 (1990)

    Article  CAS  Google Scholar 

  16. R.A. Siddiqui, P. Raj, A.K. Saxena, S.K. Dixit, Synth. React. Inorg. Met. Org. Chem. 26, 1189 (1996)

    Article  CAS  Google Scholar 

  17. S.O. Oyedemi, A.J. Afolayan, Asian Pac. J. Trop. Med. 4, 952 (2011)

    Article  CAS  Google Scholar 

  18. NCCLS/CLSI—National Committee for Clinical Laboratory Standards. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved standard document (2004), M7-A6

  19. I.P. Ejidike, P.A. Ajibade, Bioinorg. Chem. Appl. (2015). doi:10.1155/2015/890734

    Google Scholar 

  20. P. Skehan, Assays of cell growth and cytotoxicity, in Cell Growth and Apoptosis. A Practical Approach, ed. by G.P. Studzinski (Oxford University Press, Oxford, UK, 1995), pp. 169–191

    Google Scholar 

  21. K.I. Ansari, I. Hussain, H.K. Das, S.S. Mandal, FEBS J. 276, 3299 (2009)

    Article  CAS  Google Scholar 

  22. G. Venkatachalam, R. Ramesh, Spectrochim. Acta, Part A 61, 2081 (2005)

    Article  CAS  Google Scholar 

  23. R. Kaushal, S. Thakur, Chem. Eng. Trans. 32, 1801 (2013)

    Google Scholar 

  24. V.A. Shelke, S.M. Jadhav, V.R. Patharkar, S.G. Shankarwar, A.S. Munde, T.K. Chondhekar, Arabian J. Chem. 5, 501 (2012)

    Article  CAS  Google Scholar 

  25. K. Mounika, B. Anupama, J. Pragathi, C. Gyanakumari, J. Sci. Res. 2, 513 (2010)

    CAS  Google Scholar 

  26. D. Arish, M.S. Nair, J. Coord. Chem. 63, 1619 (2010)

    Article  CAS  Google Scholar 

  27. A. Braca, C. Sortino, M. Politi, I. Morelli, J. Mendez, J. Ethnopharm. 79, 379 (2002)

    Article  CAS  Google Scholar 

  28. C.P. Pandhurnekar, E.M. Meshram, H.N. Chopde, R.J. Batra, Org. Chem. Int. (2013). doi:10.1155/2013/582079

    Google Scholar 

  29. V.T. Aparadh, V.V. Naik, B.A. Karadge, Ann. Bot. (Roma) 2, 49 (2012)

    Google Scholar 

  30. J.-W. Liu, M.-X. Cai, Y. Xin, Q.-S. Wu, J. Ma, P. Yang, H.-Y. Xie, D.-S. Huang, J. Exp. Clin. Cancer Res. 29, 1 (2010)

    Article  Google Scholar 

  31. A. Ghantous, M. Saikali, T. Rau, H. Gali-Muhtasib, R. Schneider-Stock, N. Darwiche, Cancer Prev. Res. 5, 1298 (2012)

    Article  CAS  Google Scholar 

  32. K.I. Ansari, S. Kasiri, J.D. Grant, S.S. Mandal, J. Biomol. Screen. 16, 26 (2011)

    Article  CAS  Google Scholar 

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Acknowledgments

The authors would like to extend their sincere appreciation to NRF-Sasol Inzalo Foundation for funding this research.

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Correspondence to Peter A. Ajibade.

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Ejidike, I.P., Ajibade, P.A. Synthesis and in vitro anticancer, antibacterial, and antioxidant studies of unsymmetrical Schiff base derivatives of 4-[(1E)-N-(2-aminoethyl)ethanimidoyl]benzene-1,3-diol. Res Chem Intermed 42, 6543–6555 (2016). https://doi.org/10.1007/s11164-016-2479-x

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  • DOI: https://doi.org/10.1007/s11164-016-2479-x

Keywords

  • DHAP
  • Antioxidant
  • Schiff base ligands
  • Antibacterial
  • Anticancer