Table of Contents Author Guidelines Submit a Manuscript
BioMed Research International
Volume 2014 (2014), Article ID 594879, 8 pages
http://dx.doi.org/10.1155/2014/594879
Research Article

Synthesis and In Vitro Inhibition Effect of New Pyrido[2,3-d]pyrimidine Derivatives on Erythrocyte Carbonic Anhydrase I and II

1Department of Chemistry, Faculty of Art and Sciences, Sakarya University, 54140 Sakarya, Turkey
2Pamukova Vocational High School, Sakarya University, 54900 Sakarya, Turkey
3Department of Chemistry, Faculty of Art and Sciences, Balikesir University, 10145 Balikesir, Turkey

Received 21 February 2014; Revised 13 June 2014; Accepted 8 July 2014; Published 4 August 2014

Academic Editor: Anna Di Fiore

Copyright © 2014 Hilal Kuday et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. C. T. Supuran, D. Vullo, G. Manole, A. Casini, and A. Scozzafava, “Designing of novel carbonic anhydrase inhibitors and activators,” Current Medicinal Chemistry: Cardiovascular and Hematological Agents, vol. 2, no. 1, pp. 49–68, 2004. View at Publisher · View at Google Scholar · View at Scopus
  2. C. T. Supuran and A. Scozzafava, “Carbonic-anhydrase inhibitors and their therapeutic potential,” Expert Opinion on Therapeutic Patents, vol. 10, no. 5, pp. 575–600, 2000. View at Publisher · View at Google Scholar · View at Scopus
  3. D. Hewett-Emmet, “Evolution and distribution of the carbonic anhydrase gene families,” in The Carbonic Anhydrase—New Horizons, W. R. Chegwidden, Y. Edwrds, and N. Carter, Eds., pp. 29–78, Birkhäuser, Basel, Switzerland, 2000. View at Google Scholar
  4. C. T. Supuran, “Carbonic anhydrases: novel therapeutic applications for inhibitors and activators,” Nature Reviews Drug Discovery, vol. 7, no. 2, pp. 168–181, 2008. View at Publisher · View at Google Scholar · View at Scopus
  5. S. Poulsen, “Carbonic anhydrase inhibition as a cancer therapy: a review of patent literature, 2007–2009,” Expert Opinion on Therapeutic Patents, vol. 20, no. 6, pp. 795–806, 2010. View at Publisher · View at Google Scholar · View at Scopus
  6. R. J. Sundberg, Indoles, Academic Press, London, UK, 1996.
  7. M. A. H. Zahran and A. M. Ibrahim, “Synthesis and cellular cytotoxicities of new N-substituted indole-3-carbaldehyde and their indolylchalcones,” Journal of Chemical Sciences, vol. 121, no. 4, pp. 455–462, 2009. View at Publisher · View at Google Scholar · View at Scopus
  8. R. S. Chavan, H. N. More, and A. V. Bhosale, “Synthesis, characterization and evaluation of analgesic and anti-inflammatory activities of some novel indoles,” Tropical Journal of Pharmaceutical Research, vol. 10, no. 4, pp. 463–473, 2011. View at Google Scholar · View at Scopus
  9. D. Tian, G. Luo, H. Chen, X. Tang, and Y. Liu, “N-Cyclo-hexyl-2-(5-fluoro-1H-indol-3-yl)-2-oxoacetamide,” Acta Crystallographica Section E, vol. 67, no. 7, p. o1851, 2011. View at Publisher · View at Google Scholar · View at Scopus
  10. V. E. Dilli, M. Mastan, and R. T. Sobha, “Synthesis and biological evaluation of 2-aryl-3-isoxazolinyl-indole derivatives as anti-inflammatory agents,” IOSR Journal of Applied Chemistry, vol. 2, no. 3, pp. 44–49, 2012. View at Google Scholar
  11. R. S. Chavan, H. N. More, and A. V. Bhosale, “Synthesis and evaluation of analgesic and anti-inflammatory activities of a novel series of 3-(4 ,5 -dihydropyrazolyl)-indoles,” International Journal of Pharmaceutical and Biomedical Research, vol. 1, no. 4, pp. 135–143, 2010. View at Google Scholar
  12. D. Kumar, N. M. Kumar, K. Akamatsu, E. Kusaka, H. Harada, and T. Ito, “Synthesis and biological evaluation of indolyl chalcones as antitumor agents,” Bioorganic and Medicinal Chemistry Letters, vol. 20, no. 13, pp. 3916–3919, 2010. View at Publisher · View at Google Scholar · View at Scopus
  13. H. Wang and J. Zeng, “Iodine-catalyzed efficient synthesis of chalcones by grinding under solvent-free conditions,” Canadian Journal of Chemistry, vol. 87, no. 9, pp. 1209–1212, 2009. View at Publisher · View at Google Scholar · View at Scopus
  14. S. Attar, Z. O'Brien, H. Alhaddad, M. L. Golden, and A. Calderón-Urrea, “Ferrocenyl chalcones versus organic chalcones: a comparative study of their nematocidal activity,” Bioorganic and Medicinal Chemistry, vol. 19, no. 6, pp. 2055–2073, 2011. View at Publisher · View at Google Scholar · View at Scopus
  15. Z. Huang, Y. Hu, Y. Zhou, and D. Shi, “Efficient one-pot three-component synthesis of fused pyridine derivatives in ionic liquid,” ACS Combinatorial Science, vol. 13, no. 1, pp. 45–49, 2011. View at Publisher · View at Google Scholar · View at Scopus
  16. D. Q. Shi, Y. Zhou, and H. Liu, “An efficient synthesis of pyrido[2,3-d]pyrimidine derivatives in ionic liquid,” Journal of Heterocyclic Chemistry, vol. 47, no. 1, pp. 131–135, 2010. View at Publisher · View at Google Scholar · View at Scopus
  17. D. G. Powers, D. S. Casebier, D. Fokas, W. J. Ryan, J. R. Troth, and D. L. Coffen, “Automated parallel synthesis of chalcone-based screening libraries,” Tetrahedron, vol. 54, no. 16, pp. 4085–4096, 1998. View at Publisher · View at Google Scholar · View at Scopus
  18. M. G. Bursavich, N. Brooijmans, L. Feldberg et al., “Novel benzofuran-3-one indole inhibitors of PI3 kinase-α and the mammalian target of rapamycin: hit to lead studies,” Bioorganic & Medicinal Chemistry Letters, vol. 20, no. 8, pp. 2586–2590, 2010. View at Publisher · View at Google Scholar · View at Scopus
  19. A. S. El-Ahl, “Reaction of 2-oxoindolin-3-ylidene derivatives with heterocyclic enamines. A convenient one-pot synthesis of pyrimido [5,4:5',6']pyrido[2,3-b]-indole-2, 4-dione and spiro indolin-2-one-3, 5'-pyrido[2,3-d] pyrimidines,” Synthetic Communications, vol. 30, no. 12, pp. 2223–2231, 2000. View at Publisher · View at Google Scholar · View at Scopus
  20. C. Shilpa, S. Dipak, S. Vimukta, and D. Arti, “Comparative study of microwave and conventional synthesis and pharmacological activity of pyrimidines: a review,” International Journal of Pharmaceutical Sciences Review and Research, vol. 15, no. 1, pp. 15–22, 2012. View at Google Scholar · View at Scopus
  21. O. Arslan, B. Nalbantoglu, N. Demir, H. Ozdemir, and O. I. Kufrevioglu, “A new method for the purification of carbonic anhydrase isozymes by affinity chromatography,” Turkish Journal of Medical Sciences, vol. 26, no. 2, pp. 163–166, 1996. View at Google Scholar
  22. T. H. Maren, “A simplified micromethod for the determination of carbonic anhydrase and its inhibitors,” The Journal of Pharmacology and Experimental Therapeutics, vol. 130, no. 1, pp. 26–29, 1960. View at Google Scholar · View at Scopus
  23. F. Celik, M. Arslan, E. Yavuz, D. Demir, and N. Gencer, “Synthesis and carbonic anhydrase inhibitory properties of novel 1,4-dihydropyrimidinone substituted diarylureas,” Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 29, no. 1, pp. 18–22, 2014. View at Google Scholar
  24. F. Pacchiano, M. Aggarwal, B. S. Avvaru et al., “Selective hydrophobic pocket binding observed within the carbonic anhydrase II active site accommodate different 4-substituted-ureido-benzenesulfonamides and correlate to inhibitor potency,” Chemical Communications, vol. 46, no. 44, pp. 8371–8373, 2010. View at Publisher · View at Google Scholar · View at Scopus
  25. F. Pacchiano, F. Carta, P. C. McDonald et al., “Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IX and show antimetastatic activity in a model of breast cancer metastasis,” Journal of Medicinal Chemistry, vol. 54, no. 6, pp. 1896–1902, 2011. View at Publisher · View at Google Scholar · View at Scopus
  26. N. Gençer, A. Ergün, and D. Demir, “In vitro effects of some herbicides and fungicides on human erythrocyte carbonic anhydrase activity,” Fresenius Environmental Bulletin, vol. 21, no. 3, pp. 549–552, 2012. View at Google Scholar · View at Scopus
  27. D. Demir, N. Gençer, and A. Er, “Purification and characterization of prophenoloxidase from Galleria mellonella L.,” Artificial Cells, Blood Substitutes, and Biotechnology, vol. 40, no. 6, pp. 391–395, 2012. View at Publisher · View at Google Scholar · View at Scopus
  28. N. Gençer and O. Arslan, “In vitro effects of some pesticides on PON1Q192 and PON1R192 isoenzymes from human serum,” Fresenius Environmental Bulletin, vol. 20, no. 3, pp. 590–596, 2011. View at Google Scholar · View at Scopus