Skip to main content
SpringerLink
Log in

Synthesis, photophysical and antioxidant properties of carbazole-based bis-thiosemicarbazones

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Utilizing Schiff base condensation of the 9-ethylcarbazole-3,6-dicarbaldehyde and thiosemicarbazides, four new N-ethylcarbazole-based bis-thiosemicarbazone compounds 4a–d were successfully synthesized in high yields. The photophysical properties of the targeted compounds 4a–d were investigated using UV–vis absorption and fluorescence emission spectroscopy. The antioxidant properties of targeted compounds 4a–d were determined by DPPH radical scavenging, ABTS Cation Radical Decolarization and CUPRAC Cupric Reducing Antioxidant Capacity assay methods. Moreover, the anti-cholinesterase properties of designated compounds were investigated by the Acetylcholinesterase (Ach) and Butyrylcholinesterase (BCh) enzyme inhibition assays. The compound 4a was determined as a valuable candidate to be a potent antioxidant agent for the DPPH and ABTS assays. The compound 4d was found to be a target compound for the kinetic measurements to identify the mechanism of action in the area of anticholinesterase activity assay.

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

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. R.L. Hudkins, N.W. Johnson, T.S. Angeles, G.W. Gessner, J.P. Mallamo, J. Med. Chem. 50, 433 (2007)

    Article  CAS  PubMed  Google Scholar 

  2. P. Wipf, Chem. Rev. 95, 2115 (1995)

    Article  CAS  Google Scholar 

  3. A.W. Schmidt, K.R. Reddy, H.J. Knolker, Chem. Rev. 112, 3193 (2012)

    Article  CAS  PubMed  Google Scholar 

  4. H.J. Knolker, K.R. Reddy, Chem. Rev. 102, 4304 (2002)

    Article  CAS  Google Scholar 

  5. P. Rajakumar, K. Sekar, V. Shanmugaiah, N. Mathivanan, Eur. J. Med. Chem. 44, 3040 (2009)

    Article  CAS  PubMed  Google Scholar 

  6. Y. Tachibana, H. Kikuzaki, N.H. Lajis, N.J. Nakatani, Agric. Food Chem. 49, 5589 (2001)

    Article  CAS  Google Scholar 

  7. J.L. Arbiser, B. Govindarajan, T.E. Battle, R. Lynch, D.A. Frank, M. Ushio-Fukai, B.N. Perry, D.F. Stern, G.T. Bowden, A. Liu, E. Klein, P.J. Kolodziejski, N.T. Eissa, C.F. Hossain, D.G. Nagle, J. Invest. Dermatol. 126, 1396 (2006)

    Article  CAS  PubMed  Google Scholar 

  8. L. Gupta, A. Talwar, P.M. Chauhan, Curr. Med. Chem. 14, 1789 (2007)

    Article  CAS  PubMed  Google Scholar 

  9. T. Lemster, U. Pindur, G. Lenglet, S. Depauw, C. Dassi, M.H. David-Cordonnier, Eur. J. Med. Chem. 44, 3235 (2009)

    Article  CAS  PubMed  Google Scholar 

  10. M. Bingul, E. Senkuytu, M. Boga, T.N. Uslu, H. Kandemir, I.F. Sengul, Res. Chem. Intermediat. 45, 997 (2019)

    Article  CAS  Google Scholar 

  11. J.C. Mastrangelo, B.M. Conger, S.H. Chen, A. Bashir-Hashemi, Chem. Mater. 9, 227 (1997)

    Article  Google Scholar 

  12. B.M. Conger, D. Katsis, J.C. Mastrangelo, S.H. Chen, J. Phys. Chem. A 102, 9213 (1998)

    Article  CAS  Google Scholar 

  13. S.L. Lin, L.H. Chan, R.H. Lee, M.Y. Yen, W.J. Kuo, C.T. Chen, R.J. Jeng, Adv. Mater. 20, 3947 (2008)

    Article  CAS  Google Scholar 

  14. O. Ostroverkhova, W.E. Moerner, Chem. Rev. 104, 3267 (2004)

    Article  CAS  PubMed  Google Scholar 

  15. C.D. Dimitrakopoulos, R.L. Malenfant, Adv. Mater. 14, 99 (2002)

    Article  CAS  Google Scholar 

  16. K.Y. Law, Chem. Rev. 93, 449 (1993)

    Article  CAS  Google Scholar 

  17. R. Misra, T. Jadhav, B. Dhokale, P. Gautam, R. Sharma, R. Maragani, S.M. Mobin, Dalton Trans. 43, 13076 (2014)

    Article  CAS  PubMed  Google Scholar 

  18. S.O. Tümay, E. Okutan, I.F. Sengul, E. Özcan, H. Kandemir, T. Doruk, M. Çetin, B. Çoşut, Polyhedron 117, 161 (2016)

    Article  CAS  Google Scholar 

  19. E.T. Eçik, E. Özcan, H. Kandemir, I.F. Sengul, B. Çoşut, Dyes Pigm. 136, 441 (2017)

    Article  CAS  Google Scholar 

  20. P. Pawluc, A. Franczyk, J. Walkowiak, G. Hreczycho, M. Kubicki, B. Marciniec, Org. Lett. 13, 2011 (1976)

    Google Scholar 

  21. H. Kandemir, I.F. Sengul, Synth. Commun. 22, 2583 (2015)

    Article  CAS  Google Scholar 

  22. I.F. Sengul, E. Astarci, H. Kandemir, Synlett 27, 1277 (2016)

    Article  Google Scholar 

  23. R.B. de Oliveira, E.M. de Souza-Fagundes, R.P.P. Soares, A.A. Andrade, A.U. Krettli, C.L. Zani, Eur. J. Med. Chem. 43, 1983 (2008)

    Article  CAS  PubMed  Google Scholar 

  24. I. Dilovic, M. Rubcic, V. Vrdoljak, S.K. Pavelic, M. Kralj, I. Piantanida, M. Cindric, Bioorg. Med. Chem. 16, 5189 (2008)

    Article  CAS  PubMed  Google Scholar 

  25. Y. Yu, D.S. Kalinowski, Z. Kovacevic, R.A. Siafakas, P.J. Jansson, C. Stefani, D.B. Lovejoy, P.S. Sharpe, P.V. Bernhardt, D.R. Richardson, J. Med. Chem. 52, 5271 (2009)

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  27. R.F. Pavan, S.I. Maia Pedro da, R.A.S. Leite, M.V. Deflon, A.A. Batista, N.D. Sato, Eur. J. Med. Chem. 45, 1898 (2010)

    Article  CAS  PubMed  Google Scholar 

  28. W. Antholine, J. Knight, H. Whelan, D.H. Petering, Mol. Pharmacol. 13, 89 (1977)

    CAS  PubMed  Google Scholar 

  29. H.J. Zhang, Y. Qian, D.D. Zhu, X.G. Yang, H.L. Zhu, Eur. J. Med. Chem. 46, 4702 (2011)

    Article  CAS  PubMed  Google Scholar 

  30. K. Hu, Z.H. Yang, S.S. Pan, H.J. Xu, J. Ren Eur. J. Med. Chem. 45, 3453 (2010)

    Article  CAS  Google Scholar 

  31. R. Gust, I. Ott, D. Posselt, K. Sommer, J. Med. Chem. 47, 5837 (2004)

    Article  CAS  PubMed  Google Scholar 

  32. A. Garoufis, S.K. Hadjikakou, N. Hadjiliadis, Coord. Chem. Rev. 253, 1384 (2009)

    Article  CAS  Google Scholar 

  33. 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 

  34. P.F. Salas, C. Herrmann, C. Orvig, Chem. Rev. 113, 3450 (2013)

    Article  CAS  PubMed  Google Scholar 

  35. A.S. Hosseini-Yazdi, A. Mirzaahmadi, A.A. Khandar, V. Eigner, M. Dušek, M. Mahdavi, S. Soltani, F. Lotfipour, J. White, Polyhedron 124, 156 (2017)

    Article  CAS  Google Scholar 

  36. Z. Piri, Z. Moradi-Shoeili, A. Assoud, Inorg. Chem. Commun. 84, 122 (2017)

    Article  CAS  Google Scholar 

  37. D. Palanimuthu, R. Poon, S. Sahni, R. Anjum, D. Hibbs, H.Y. Lin, V.P. Bernhardt, D.S. Kalinowski, D.R. Richardson, Eur. J. Med. Chem. 139, 612 (2017)

    Article  CAS  PubMed  Google Scholar 

  38. L. Yu, L. Li, X. Fei, J. Lumin. 149, 28 (2014)

    Article  CAS  Google Scholar 

  39. M.S. Blois, Nature 181, 1199 (1958)

    Article  CAS  Google Scholar 

  40. R. Re, N. Pellegrini, A. Proteggente, A. Pannala, M. Yang, C. Rice-Evans, Free Radical Biol. Med. 26, 1231 (1999)

    Article  CAS  Google Scholar 

  41. R. Apak, K. Güçlü, M. Özyürek, S.E. Karademir, J. Agric. Food Chem. 52, 7970 (2004)

    Article  CAS  PubMed  Google Scholar 

  42. G.L. Ellman, K.D. Courtney, V. Andres, R.M. Featherston, Biochem. Pharmacol. 7, 88 (1961)

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

I thank the Dicle University Scientific Research Project Coordinator (DUBAP Project Number: ECZ 15.007) for the financial support given to the research project.

Author information

Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Dicle University, Diyarbakır, 21280, Turkey

    Murat Bingul

  2. Department of Chemistry, Faculty of Science, Gebze Technical University, Gebze, Kocaeli, Turkey

    Elif Şenkuytu, Mehmet F. Saglam & Ibrahim F. Sengul

  3. Department of Pharmaceutical Technology, Faculty of Pharmacy, Dicle University, Diyarbakır, 21280, Turkey

    Mehmet Boga

  4. Department of Chemistry, Faculty of Art and Science, Namık Kemal University, Tekirdag, Turkey

    Hakan Kandemir

Authors
  1. Murat Bingul
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Elif Şenkuytu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mehmet F. Saglam
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Mehmet Boga
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Hakan Kandemir
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Ibrahim F. Sengul
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ibrahim F. Sengul.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 1825 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bingul, M., Şenkuytu, E., Saglam, M.F. et al. Synthesis, photophysical and antioxidant properties of carbazole-based bis-thiosemicarbazones. Res Chem Intermed 45, 4487–4499 (2019). https://doi.org/10.1007/s11164-019-03844-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-019-03844-x

Keywords

Search

Navigation