Skip to main content
SpringerLink
Log in

Novel iminocoumarin imidazo[4,5-b]pyridine derivatives: design, synthesis, and biological evaluation

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Herein, we present the design, synthesis, and biological activity of novel iminocoumarin imidazo[4,5-b]pyridine derivatives. The prepared compounds were designed to study the type of substituent in position 6 of the coumarin nucleus as well as the type of the substituent at the N atom of imidazo[4,5-b]pyridine core for their effect on the biological activity. Therefore, all compounds were tested for their antiproliferative action on several human cancer cell lines in vitro, for their antioxidative activity, antibacterial activity on several bacterial strains, and for their antiviral activity on several viruses. The results of the evaluation of biological activity revealed that the tested derivatives did not display significant biological activities. The majority of the tested compounds were not active at all, while some derivatives showed low activity in these assays. Therefore, we could conclude that the biological potential of 6-substituted iminocoumarin derivatives is very low – the substitution in position 6 of the coumarin nucleus, in comparison to 7-substituted iminocoumarins, strongly decreases biological activity.

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

Figure 1.
Scheme 1.

Similar content being viewed by others

References

  1. Sandhu, S.; Bansal, Y.; Silakari, O.; Bansal, G. Bioorg. Med. Chem. 2015, 22, 3806.

    Article  Google Scholar 

  2. Song, X.-F.; Fan, J.; Liu, L.; Liu, X.-F.; Gao, F. Arch. Pharm. 2020, 353, 2000025..

    Article  CAS  Google Scholar 

  3. Prusty, J. S.; Kumar, A. Mol. Diversity 2020, 24, 1367.

    Article  CAS  Google Scholar 

  4. Li, H.; Cai, L.; Chen Z. In Advances in Chemical Sensors; Wang, W., Ed.; InTech: Rijeka, 2011, p.121.

  5. Khemakhem, K.; Ammar, H.; Abid, S.; El Gharbi, R.; Fery-Forgues, S. Dyes Pigm. 2013, 99, 594.

    Article  CAS  Google Scholar 

  6. Sinha, S.; Singh, K.; Ved, A.; Hasan, S. M.; Mujeeb, S. Mini- Rev. Med. Chem. 2022, 22, 1314.

    CAS  Google Scholar 

  7. Murray, R. D. H.; Mendez, J.; Brown, S. A. The Natural Coumarins: Ocurrence, Chemistry and Biochemistry; Wiley: Chichester, 1982.

  8. Sharifi-Rad, J.; Cruz-Martins, N.; López-Jornet, P.; Pons-Fuster Lopez, E.; Harun, N.; Yeskaliyeva, B.; Beyatli, A.; Sytar, O.; Shaheen, S.; Sharopov, F.; Taheri, Y.; Docea, A. O.; Calina, D.; Cho, W. C. Oxid. Med. Cell. Longevity 2021, 6492346.

  9. Roussaki, M.; Kontogiorgis, C. A.; Hadjipavlou-Litina, D.; Hamilakis, S.; Detsi, A. Bioorg. Med. Chem. Lett. 2020, 20, 3889.

    Article  Google Scholar 

  10. Prusty, J. S.; Kumar, A. Mol. Diversity 2020, 24, 1367.

    Article  CAS  Google Scholar 

  11. Carneiro, A.; Matos, M. J.; Uriarte, E.; Santana, L. Molecules 2021, 26, 501.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Tsay, S.-C.; Lin, S.-Y.; Huang, W.-C.; Hsu, M.-H.; Hwang, K. C.; Lin, C.-C.; Horng, J.-C.; Chen, I.-C.; Hwu, J. R.; Shieh, F.-K.; Leyssen, P.; Neyts, J. Molecules 2016, 21, 228.

    Article  PubMed  PubMed Central  Google Scholar 

  13. Feng, D.; Zhang, A.; Yang, Y.; Yang, P. Arch. Pharm. 2020, 353, 1900380.

    Article  CAS  Google Scholar 

  14. Emami, S.; Dadashpour, S. Eur. J. Med. Chem. 2015, 102, 611.

    Article  CAS  PubMed  Google Scholar 

  15. Thakur, A.; Singla, R.; Jaitak, V. Eur. J. Med. Chem. 2015, 101, 476.

    Article  CAS  PubMed  Google Scholar 

  16. Silverman, R. B. The Organic Chemistry of Drug Design and Drug Action; Elsevier Academic Press: Amsterdam, 2004, 2nd ed.

  17. Dorababu, A. Eur. J. Med. Chem. Rep. 2021, 2, 100006.

    CAS  Google Scholar 

  18. Zhang, L.; Xu, Z. Eur. J. Med. Chem. 2019, 181, 111587.

    Article  CAS  PubMed  Google Scholar 

  19. Gabr, M. T.; Ibrahim, M. M. H.; Tripathi, A.; Prabhakar, C. Chemosensors 2019, 7, 34.

    Article  CAS  Google Scholar 

  20. Dai, M.; Sarkar, S.; Song, C. W.; Reo, Y. J.; Yang, Y. J.; Ahn, K. H. ChemPhotoChem 2020, 4, 721.

    Article  CAS  Google Scholar 

  21. Chemate, S. B.; Sekar, N. J. Fluoresc. 2015, 25, 1615.

    Article  CAS  PubMed  Google Scholar 

  22. Abid-Jarraya, N.; Khemakhem, K.; Turki-Guermazi, H.; Abid, S.; Saffon, N.; Fery-Forgues, S. Dyes Pigm. 2016, 132, 177.

    Article  CAS  Google Scholar 

  23. Perin, N.; Cindrić, M.; Vervaeke, P.; Liekens, S.; Mašek, T.; Starčević, K.; Hranjec, M. Med. Chem. (Sharjah, United Arab Emirates) 2021, 17, 13.

  24. Boček, I.; Hranjec, M.; Vianello, R. J. Mol. Liq. 2022, 355, 118982.

    Article  Google Scholar 

  25. Boček, I.; Starčević, K.; Novak Jovanović, I.; Vianello, R.; Hranjec, M. J. Mol. Liq. 2021, 342, 117527.

    Article  Google Scholar 

  26. Vasylevska, A. S.; Karasyov, A. A.; Borisov, S. M.; Krause, C. Anal. Bioanal. Chem. 2007, 387, 2131.

    Article  CAS  PubMed  Google Scholar 

  27. Boček Pavlinac, I.; Zlatić, K.; Persoons, L.; Daelemans, D.; Banjanac, M.; Radovanović, V.; Butković, K.; Kralj, M.; Hranjec, M. Molecules 2023, 28, 34.

    Article  Google Scholar 

  28. (a) Grgičević, I.; Mikulandra, I.; Bukvić, M.; Banjanac, M.; Radovanović, V.; Habinovec, I.; Bertoša, B.; Novak, P. Int. J. Antimicrob. Agents 2020, 56, 106147. (b) https://clsi.org/

  29. Perin, N.; Roškarić, P.; Sović, I.; Boček, I.; Starčević, K.; Hranjec, M.; Vianello, R. Chem. Res. Toxicol. 2018, 31, 974.

    Article  CAS  PubMed  Google Scholar 

  30. Cindrić, M.; Sović, I.; Mioč, M.; Hok, L.; Boček, I.; Roškarić, P.; Butković, K.; Martin-Kleiner, I.; Starčević, K.; Vianello, R.; Kralj, M.; Hranjec, M. Antioxidants 2019, 8, 477.

    Article  PubMed  PubMed Central  Google Scholar 

  31. Gülçin, I.; Huyut, Z.; Elmastas, M.; Aboul-Enein, H. Y. Arab. J. Chem. 2010, 3, 43.

    Article  Google Scholar 

  32. Beč, A.; Racané, L.; Žonja, L.; Persoons, L.; Daelemans, D.; Starčević, K.; Vianello, R.; Hranjec, M. RSC Med. Chem. 2023, 14, 957.

    Article  PubMed  PubMed Central  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, HR-10000, Zagreb, Croatia

    Ida Boček Pavlinac & Marijana Hranjec

  2. Department of Chemistry and Biochemistry, Faculty of Veterinary Medicine, University of Zagreb, Heinzelova 55, HR-10000, Zagreb, Croatia

    Kristina Starčević

  3. KU Leuven, Department of Microbiology, Immunology and Transplantation, Rega Institute, Leuven, Belgium

    Leentje Persoons & Dirk Daelemans

  4. Pharmacology in vitro, Selvita Ltd., Prilaz baruna Filipovića 29, 10000, Zagreb, Croatia

    Mihailo Banjanac & Vedrana Radovanović

Authors
  1. Ida Boček Pavlinac
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Kristina Starčević
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Leentje Persoons
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Mihailo Banjanac
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Vedrana Radovanović
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Dirk Daelemans
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Marijana Hranjec
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Marijana Hranjec.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2024, 60(1/2), 75–82

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (PDF 3800 kb)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Pavlinac, I.B., Starčević, K., Persoons, L. et al. Novel iminocoumarin imidazo[4,5-b]pyridine derivatives: design, synthesis, and biological evaluation. Chem Heterocycl Comp 60, 75–82 (2024). https://doi.org/10.1007/s10593-024-03296-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-024-03296-1

Keywords

Search

Navigation