Please check captured article title, if appropriate."/> Skip to main content
SpringerLink
Log in

In a search for selective inhibitors of carbonic anhydrases: coumarin and its bioisosteres – synthesis and derivatization

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

This review describes the preparation and derivatization of coumarin and its bioisosteres – thioxocoumarin, thiocoumarin, dithiocoumarin, and sulfocoumarin derivatives triggered by natural product and utilized in the investigation of inhibitors of carbonic anhydrases with a focus on cancer-associated isoforms of carbonic anhydrases.

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
Figure 2

Similar content being viewed by others

References

  1. Supuran, C. T. Nat. Rev. Drug Discovery 2008, 7, 168.

    Article  CAS  Google Scholar 

  2. Alterio, V.; Di Fiore, A.; D'Ambrosio, K.; Supuran C. T.; De Simone, G. Chem. Rev. 2012, 112, 4421.

    Article  CAS  Google Scholar 

  3. Guler, O. O.; De Simone, G.; Supuran, C. T. Curr. Med. Chem. 2010, 17, 1516.

    Article  CAS  Google Scholar 

  4. Vu, H.; Pham, N. B.; Quinn, R. J. J. Biomol. Screen. 2008, 13, 265.

    Article  CAS  Google Scholar 

  5. Maresca, A.; Temperini, C.; Vu, H.; Pham, N. B.; Poulsen, S. A.; Scozzafava, A.; Quinn, R. J.; Supuran, C. T. J. Am. Chem. Soc. 2009, 131, 3057.

    Article  CAS  Google Scholar 

  6. Davis, R. A.; Vullo, D.; Maresca, A.; Supuran, C. T.; Poulsen, S. A. Bioorg. Med. Chem. 2013, 21, 1539.

    Article  CAS  Google Scholar 

  7. Maresca, A.; Temperini, C.; Pochet, L.; Masereel, B.; Scozzafava, A.; Supuran, C. T. J. Med. Chem. 2010, 53, 335.

    Article  CAS  Google Scholar 

  8. Pochet, L.; Doucet, C.; Schynts, M.; Thierry, N.; Boggetto, N.; Pirotte, B.; Jiang, K. Y.; Masereel, B.; de Tullio, P.; Delarge, J.; Reboud-Ravaux, M. J. Med. Chem. 1996, 39, 2579.

    Article  CAS  Google Scholar 

  9. Robert, S.; Bertolla, C.; Masereel, B.; Dogné, J.-M.; Pochet, L. J. Med. Chem. 2008, 51, 3077.

    Article  CAS  Google Scholar 

  10. Doucet, C.; Pochet, L.; Thierry, N.; Pirotte, B.; Delarge, J.; Reboud-Ravaux, M. J. Med. Chem. 1999, 42, 4161.

    Article  CAS  Google Scholar 

  11. Symeonidis, T.; Chamilos, M.; Hadjipavlou-Litina, D. J.; Kallitsakis, M.; Litinas, K. E. Bioorg. Med. Chem. Lett. 2009, 19, 1139.

    Article  CAS  Google Scholar 

  12. Maresca, A.; Scozzafava, A.; Supuran, C. T. Bioorg. Med. Chem. Lett. 2010, 20, 7255.

    Article  CAS  Google Scholar 

  13. Sharma, A.; Tiwari, M.; Supuran, C. T. J. Enzyme Inhib. Med. Chem. 2014, 29, 292.

    Article  CAS  Google Scholar 

  14. Winum, J.-Y.; Casini, A.; Mincione, F.; Starnotti, M.; Montero, J.-L.; Scozzafava, A.; Supuran, C. T. Bioorg. Med. Chem. Lett. 2004, 14, 225.

    Article  CAS  Google Scholar 

  15. Wilkinson, B. L.; Bornaghi, L. F.; Houston, T. A.; Innocente, A.; Supuran, C. T.; Poulsen, S. A. J. Med. Chem. 2006, 49, 6539.

    Article  CAS  Google Scholar 

  16. Wilkinson, B. L.; Bornaghi, L. F.; Houston, T. A.; Innocenti, A.; Vullo, D.; Supuran, C. T.; Poulsen, S. A. J. Med. Chem. 2007, 50, 1651.

    Article  CAS  Google Scholar 

  17. Wilkinson, B. L.; Innocenti, A.; Vullo, D.; Supuran, C. T.; Poulsen, S. A. J. Med. Chem. 2008, 51, 1945.

    Article  CAS  Google Scholar 

  18. Touisni, N.; Maresca, A.; McDonald, P. C.; Lou, Y.; Scozzafava, A.; Dedhar, S.; Winum, J.-Y.; Supuran, C. T. J. Med. Chem. 2011, 54, 8271.

    Article  CAS  Google Scholar 

  19. Carta, F.; Maresca, A.; Scozzafava, A.; Supuran, C. T. Bioorg. Med. Chem. 2012, 20, 2266.

    Article  CAS  Google Scholar 

  20. Supuran, C.; Dedhar, S.; Carta, F.; Winum, J.-Y.; McDonald, P. C. WO Patent 2012070024.

  21. Zhong, P.; Xiong, Z. X.; Huang, X. Synth. Commun. 2000, 30, 2793.

    Article  CAS  Google Scholar 

  22. Meth-Cohn, O.; Tarnowski, B. Synthesis 1978, 56.

  23. Grandane, A.; Belyakov, S.; Trapencieris, P.; Zalubovskis, R. Tetrahedron 2012, 68, 5541.

    Article  CAS  Google Scholar 

  24. Grandāne, A.; Mishnev, A. F.; Vozny, I. V.; Žalubovskis R. Chem. Heterocycl. Compd. 2012, 48, 974. [Khim. Geterotsikl. Soedin. 2012, 1044.]

  25. Tars, K.; Vullo, D.; Kazaks, A.; Leitans, J.; Lends, A.; Grandane, A.; Zalubovskis, R.; Scozzafava, A.; Supuran C. T. J. Med. Chem. 2013, 56, 293.

    Article  CAS  Google Scholar 

  26. Grandane, A.; Tanc, M.; Zalubovskis, R.; Supuran, C. T. Bioorg. Med. Chem. Lett. 2014, 24, 1256.

    Article  CAS  Google Scholar 

  27. Špulák, M.; Lubojacký, R.; Šenel, P.; Kuneš, J.; Pour, M. J. Org. Chem. 2010, 75, 241.

    Article  Google Scholar 

  28. Grandane, A.; Tanc, M.; Zalubovskis, R.; Supuran, C. T. Bioorg. Med. Chem. 2014, 22, 1522.

    Article  CAS  Google Scholar 

  29. Grandane, A.; Tanc, M.; Žalubovskis, R.; Supuran, C. T. Bioorg. Med. Chem. 2015, 23, 1430.

    Article  CAS  Google Scholar 

  30. Grandane, A.; Tanc, M.; Di Cesare Mannelli, L.; Carta, F.; Ghelardini, C.; Žalubovskis, R.; Supuran, C. T. J. Med. Chem. 2015, 58, 3975.

    Article  CAS  Google Scholar 

  31. Tanc, M.; Carta, F.; Bozdag, M.; Scozzafava, A.; Supuran, C. T. Bioorg. Med. Chem. 2013, 21, 4502.

    Article  CAS  Google Scholar 

  32. Tanc, M.; Carta, F.; Scozzafava, A.; Supuran, C. T. Org. Biomol. Chem. 2015, 13, 77.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Latvian Institute of Organic Synthesis, 21 Aizkraukles St, Riga, LV-1006, Latvia

    Raivis Žalubovskis

Authors
  1. Raivis Žalubovskis
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Raivis Žalubovskis.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(7), 607–612

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Žalubovskis, R. In a search for selective inhibitors of carbonic anhydrases: coumarin and its bioisosteres – synthesis and derivatization. Chem Heterocycl Comp 51, 607–612 (2015). https://doi.org/10.1007/s10593-015-1748-8

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-015-1748-8

Keywords

Search

Navigation