Log in

New Zn(II) Complexes of Pyrazole-Based Ligands: Synthesis, Characterization, and Inhibition of the Activity of Isoenzymes of Carbonic Anhydrase

  • Published:
Pharmaceutical Chemistry Journal Aims and scope

Two new Zn(II) complexes of (4-benzoyl-1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3-carbonyl)(5-sulfamoyl- 1,3,4-thiadiazol-2-yl)amide (L1) and (4-(ethoxycarbonyl)-1,5-diphenyl-1H-pyrazole-3-carbonyl)(5-sulfa- moyl-1,3,4-thiadiazol-2-yl)amide (L2) were synthesized. Characterization of the structure of complexes was performed using spectroscopic methods, elemental analysis, and magnetic moments. The inhibitory effects of acetazolamide (AAZ) as the control compound, free ligands (L1 and L2), and newly synthesized Zn(II) (1 and 2) complexes on hCA I and hCA II isoenzymes were investigated in vitro and IC50 values (the concentration of inhibitor producing a 50% inhibition of carbonic anhydrase activity) were compared. It was found that the in- hibitory effects of the synthesized complexes against hCA I and hCA II were greater than AAZ but slightly lower than free ligands.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1.

Similar content being viewed by others

References

  1. C. T. Supuran, Biochem. J., 473(14), 2023 – 2032 (2016).

    Article  CAS  PubMed  Google Scholar 

  2. C. T. Supuran, C. Capasso, Pathogens, 6(3), 30 (2017).

    Article  PubMed  PubMed Central  Google Scholar 

  3. C. Campestre, V. De Luca, S. Carradori, et al., Front. Microbiol., 12, 629163 (2021).

    Article  PubMed  PubMed Central  Google Scholar 

  4. C. T. Supuran, Expert Opin. Ther. Pat., 28(10), 709 – 712 (2018).

    Article  CAS  PubMed  Google Scholar 

  5. S. Del Prete, S. Bua, F. A. S. Alasmary, et al., Mar. Drugs, 17(3), 146 (2019).

    Article  PubMed  PubMed Central  Google Scholar 

  6. N. Buyukkidan, B. Buyukkidan, M. Bulbul, et al., J. Enzyme Inhib. Med. Chem., 32(1), 208 – 213 (2017).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. P. Taslimi, I. Gulcin, N. Oztaskin, et al., J. Enzyme Inhib. Med. Chem., 31(4), 603 –607 (2016).

    Article  CAS  PubMed  Google Scholar 

  8. A. Angeli, V. Kartsev, A. Petrou, et al., Pharmaceuticals, 14(8), 828 (2021).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. C. T. Supuran, Nat. Rev. Drug Discovery, 7(2), 168 – 181 (2008).

    Article  CAS  PubMed  Google Scholar 

  10. C. T. Supuran, Expert Opin. Drug Discovery, 15(6), 671 – 686 (2020).

    Article  CAS  Google Scholar 

  11. C. T. Supuran, Curr. Top. Med. Chem., 7(9), 825 – 833 (2007).

    Article  CAS  PubMed  Google Scholar 

  12. M. Aggarwal, B. Kondeti, R. McKenna, Bioorg. Med. Chem., 21(6), 1526 – 1533 (2013).

    Article  CAS  PubMed  Google Scholar 

  13. K. S. Kumar, N. P. Priya, K. K. Aravindakshan, Pharm. Chem. J., 54(10), 1079 – 1086 (2021).

    Article  CAS  Google Scholar 

  14. S. Mert, Z. Alim, M. M. Isgor, et al., Arabian J. Chem., 12(8), 2740 – 2748 (2019).

    Article  CAS  Google Scholar 

  15. C. T. Supuran, Met.-Based Drugs, 2(6), 327 – 330 (1995).

  16. A. Scozzafava, C. T. Supuran, Met.-Based Drugs, 4(1), 19 – 26 (1997).

  17. S. L. Sumalan, J. Casanova, G. Alzuet, et al., J. Inorg. Biochem., 62(1), 31 – 39 (1996).

    Article  CAS  PubMed  Google Scholar 

  18. J. Borràs, T. Cristea, C. T. Supuran, Main Group Met. Chem., 19(6), 339 – 346 (1996).

    Article  Google Scholar 

  19. G. Mincione, A. Scozzafava, C. T. Supuran, Met.-Based Drugs, 4(1), 27 – 34 (1997).

  20. J. Borràs, J. Casanova, T. Cristea, et al., Met.-Based Drugs, 3(3), 143 – 148 (1996).

  21. F. K. Keter, J. Darkwa, BioMetals, 25(1), 9 – 21 (2012).

    Article  CAS  PubMed  Google Scholar 

  22. M. Bulbul, R. Kasimogullari, O. I. Kufrevioglu, J. Enzyme Inhib. Med. Chem., 23(6), 895 – 900 (2008).

    Article  CAS  PubMed  Google Scholar 

  23. O. Arslan, B. Nalbantoglu, N. Demir, et al., Turk. J. Med. Sci., 26(2), 163 – 166 (1996).

    CAS  Google Scholar 

  24. M. M. Bradford, Anal Biochem., 72(1 – 2), 248 – 254 (1976).

    Article  CAS  PubMed  Google Scholar 

  25. U. K. Laemmli, Nature, 227(5259), 680 – 685 (1970).

    Article  CAS  PubMed  Google Scholar 

  26. K. M.Wilbur, N. G. Anderson, J. Biol. Chem., 176(1), 147 – 154 (1948).

    Article  CAS  PubMed  Google Scholar 

  27. C. Landolfi, M. Marchetti, G. Ciocci, C. Milanese, J. Pharmacol. Toxicol. Methods, 38(3), 169 – 172 (1997).

    Article  CAS  PubMed  Google Scholar 

  28. M. Bulbul, O. Hisar, S. Beydemir, et al., J. Enzyme Inhib. Med. Chem., 18(4), 371 – 375 (2003).

    Article  PubMed  Google Scholar 

  29. M. Ciftci, M. Bulbul, M. Gul, et al., J. Enzyme Inhib. Med. Chem., 20(1), 103 – 108 (2005).

    Article  CAS  PubMed  Google Scholar 

  30. O. Hisar, S. Beydemir,M. Bulbul, T. Yanik, J. Appl. Anim. Res., 30(2), 185 – 188 (2006).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to N. Büyükkıdan.

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

Bülbül, M., Büyükkıdan, N., Kasımoğulları, R. et al. New Zn(II) Complexes of Pyrazole-Based Ligands: Synthesis, Characterization, and Inhibition of the Activity of Isoenzymes of Carbonic Anhydrase. Pharm Chem J 57, 987–991 (2023). https://doi.org/10.1007/s11094-023-02975-1

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11094-023-02975-1

Keywords

Navigation