Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2014 (2014), Article ID 126323, 8 pages
http://dx.doi.org/10.1155/2014/126323
Research Article

Synthesis of 1,8-Naphthyridine Derivatives under Ultrasound Irradiation and Cytotoxic Activity against HepG2 Cell Lines

1Chemistry Department, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia
2Medicinal Chemistry Department, National Research Center, Dokki, Cairo 12622, Egypt

Received 4 December 2013; Revised 27 January 2014; Accepted 27 January 2014; Published 12 March 2014

Academic Editor: Angelo de Fatima

Copyright © 2014 N. S. Ahmed 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. S. Massari, D. Daelemans, M. L. Barreca et al., “A 1,8-naphthyridone derivative targets the HIV-1 Tat-mediated transcription and potently inhibits the HIV-1 replication,” Journal of Medicinal Chemistry, vol. 53, no. 2, pp. 641–648, 2010. View at Publisher · View at Google Scholar · View at Scopus
  2. A. A. Fadda, A. M. El-Defrawy, and S. A. El-Habiby, “Synthesis, cytotoxicity activity, DFT molecular modeling studies and quantitative structure activity relationship of some novel 1, 8-naphthyridine derivatives,” The American Journal of Organic Chemistry, vol. 2, no. 4, pp. 87–96, 2012. View at Google Scholar
  3. G. Roma and G. Grossi, “1, 8-naphthyridines VII. New substituted 5-amino[1, 2, 4]triazolo[4, 3-a][1, 8]naphthyridine-6-carboxamides and their isosteric analogues, exhibiting notable anti-inflammatory and/or analgesic activities, but no acute gastrolesivity,” European Journal of Medicinal Chemistry, vol. 43, no. 8, pp. 1665–1680, 2008. View at Google Scholar
  4. S. Olepu and P. K. Suryadevara, “2-Oxo-tetrahydro-1, 8-naphthyridines as selective inhibitors of malarial protein farnesyltransferase and as anti-malarials,” Bioorganic and Medicinal Chemistry Letters, vol. 18, no. 2, pp. 494–497, 2008. View at Google Scholar
  5. E. Laxminarayana, T. Karunakar, S. S. Shankar, and M. T. Chary, “A study on antibacterial activity of substituted 1, 8-naphthyridines containing carbaldehydes, methyleden hydrazines, thiadiazolamines and triazolethiols,” Advanced Drug Delivery Reviews, vol. 2, no. 2, pp. 6–11, 2012. View at Google Scholar
  6. J. M. Quintela and C. Peinador, “Piperazine N-substituted naphthyridines, pyridothienopyrimidines and pyridothienotriazines: new antiprotozoals active against Philasterides dicentrarchi,” European Journal of Medicinal Chemistry, vol. 38, no. 3, pp. 265–275, 2003. View at Google Scholar
  7. T. Aboul-Fadl, F. A. S. Bin-Jubair, and O. Aboul-Wafa, “Schiff bases of indoline-2,3-dione (isatin) derivatives and nalidixic acid carbohydrazide, synthesis, antitubercular activity and pharmacophoric model building,” European Journal of Medicinal Chemistry, vol. 45, no. 10, pp. 4578–4586, 2010. View at Publisher · View at Google Scholar · View at Scopus
  8. P. L. Ferrarini, C. Mori, M. Badawneh et al., “Synthesis and antiplatelet activity of some 3-phenyl-1, 8-naphthyridine derivatives,” Farmaco, vol. 55, no. 9-10, pp. 603–610, 2000. View at Publisher · View at Google Scholar · View at Scopus
  9. V. Kren and T. Renzanak, “Sweet antibiotics: the role of glycosidic residues in antibiotic and antitumor activity and their randomization,” FEMS Microbiology Reviews, vol. 32, no. 5, pp. 858–889, 2008. View at Google Scholar
  10. V. Kren and L. Martínková, “Glycosides in medicine: the role of glycosidic residue in biological activity,” Medicinal Chemistry Reviews, vol. 8, pp. 1313–1338, 2001. View at Google Scholar
  11. Y. Tsuzuki, K. Tomita, K. Shbamori, Y. Sato, S. Kashimoto, and K. Chiba, “Synthesis and Ssructure-activity relationships of novel 7-substituted 1, 4-dihydro-4-oxo-1-(2-thiazolyl)-1, 8-naphthyridine-3-carboxylic acids as antitumor agents. Part 2,” Journal of Medicinal Chemistry, vol. 47, no. 8, pp. 2097–2109, 2004. View at Google Scholar
  12. D. A. Burden and N. Oshereoff, “Mechanism of action of eukaryotic topoisomerase II and drugs targeted to the enzyme,” Biochimica et Biophysica Acta, vol. 1400, no. 1–3, pp. 139–154, 1998. View at Google Scholar
  13. A. F. Eweas, N. M. Khalifa, N. S. Ismail, I. M. A. Al-Omar, and A. M. Soliman, “Synthesis, molecular docking of novel 1, 8-naphthyridine derivatives and their cytotoxic activity against HepG2 cell lines,” Medicinal Chemistry Research, vol. 23, no. 1, pp. 76–86, 2014. View at Google Scholar
  14. A. M. Farag, A. S. Mayhoub, S. E. Barakat, and A. H. Bayomi, “Regioselective synthesis and antitumor screening of some novel N-phenylpyrazole derivatives,” Bioorganic and Medicinal Chemistry, vol. 16, no. 2, pp. 881–889, 2008. View at Publisher · View at Google Scholar · View at Scopus
  15. S. Huang, R. Lin, Y. Yu et al., “Synthesis of 3-(1H-benzimidazol-2-yl)-5-isoquinolin-4-ylpyrazolo[1, 2-b]pyridine, a potent cyclin dependent kinase 1 (CDK1) inhibitor,” Bioorganic and Medicinal Chemistry Letters, vol. 17, no. 5, pp. 1243–1245, 2007. View at Google Scholar
  16. W. Rzeski, J. Matysiak, and M. Kandefer-Szerszen, “Anticancer, neuroprotective activities and computational studies of 2-amino-1, 3, 4-thiadiazole based compound,” Bioorganic and Medicinal Chemistry, vol. 15, no. 9, pp. 3201–3207, 2007. View at Google Scholar
  17. J.-Y. Chou, S.-Y. Lai, S.-L. Pan, G.-M. Jow, J.-W. Chern, and J.-H. Guh, “Investigation of anticancer mechanism of thiadiazole-based compound in human non-small cell lung cancer A549 cells,” Biochemical Pharmacology, vol. 66, no. 1, pp. 115–124, 2003. View at Publisher · View at Google Scholar · View at Scopus
  18. M. R. Yadav, S. T. Shirude, D. S. Puntambekar et al., “Studies in 3,4-diaryl-1,2,5-oxadiazoles and their N-oxides: search for better COX-2 inhibitors,” Acta Pharmaceutica, vol. 57, no. 1, pp. 13–30, 2007. View at Publisher · View at Google Scholar · View at Scopus
  19. G. Cravotto and P. Cintas, “Power ultrasound in organic synthesis: moving cavitational chemistry from academia to innovative and large-scale applications,” Chemical Society Reviews, vol. 35, pp. 180–196, 2006. View at Google Scholar
  20. L. Pizzuti, P. L. G. Martins, B. A. Ribeiro et al., “Efficient sonochemical synthesis of novel 3,5-diaryl-4,5-dihydro-1H-pyrazole-1-carboximidamides,” Ultrasonics Sonochemistry, vol. 17, no. 1, pp. 34–37, 2010. View at Publisher · View at Google Scholar · View at Scopus
  21. Z. Fu and H. Shao, “An efficient synthesis of 3-substituted indole derivates under ultrasound irradiation,” Ultrasonics Sonochemistry, vol. 18, no. 2, pp. 520–526, 2011. View at Publisher · View at Google Scholar · View at Scopus
  22. Q. Liu, H. Ai, and Z. Li, “Potassium sorbate as an efficient and green catalyst for Knoevenagel condensation,” Ultrasonics Sonochemistry, vol. 18, no. 2, pp. 477–479, 2011. View at Google Scholar
  23. K. Jadidi, R. Gharemanzadeh, M. Mehrdad, H. R. Darabi, H. R. Khavasi, and D. Asgari, “A facile synthesis of novel pyrrolizidines under classical and ultrasonic conditions,” Ultrasonics Sonochemistry, vol. 15, no. 2, pp. 124–128, 2008. View at Publisher · View at Google Scholar · View at Scopus
  24. M. R. Shaaban, T. S. Saleh, A. S. Mayhoub, and A. M. Farag, “Single step synthesis of new fused pyrimidine derivatives and their evaluation as potent Aurora-A kinase inhibitors,” European Journal of Medicinal Chemistry, vol. 46, no. 9, pp. 3690–3695, 2011. View at Publisher · View at Google Scholar · View at Scopus
  25. M. Mokhtar, T. S. Saleh, N. S. Ahmed, S. A. Al-Thabaiti, and R. A. Al-Shareef, “An eco-friendly N-sulfonylation of amines using stable and reusable Zn-Al-hydrotalcite solid base catalyst under ultrasound irradiation,” Ultrasonics Sonochemistry, vol. 18, no. 1, pp. 172–176, 2011. View at Publisher · View at Google Scholar · View at Scopus
  26. N. S. Ahmed, T. S. Saleh, and E. H. El-Mossalamy, “An efficiently sonochemical synthesis of novel pyrazoles, bipyrazoles and pyrazol-3- ylPyrazolo[3,4-d]pyrimidines incorporating 1H-benzoimidazole Moiety,” Current Organic Chemistry, vol. 17, pp. 194–202, 2013. View at Google Scholar
  27. N. S. Ahmed, K. O. Alfooty, and S. S. Khalifah, “An efficient sonochemical synthesis of novel Schiff 's bases, thiazolidine and Pyrazolidine Incorporating 1, 8-NaphthyridineMoiety and their cytotoxic activity against HePG2 cell lines,” Scientific World Journal, vol. 2014, Article ID 587059, 10 pages, 2014. View at Publisher · View at Google Scholar
  28. N. Cabello, P. Cintas, and J. L. Luche, “sonochemical effects in the additions of furan to masked Ortho benzoquinone,” Ultrasonics Sonochemistry, vol. 10, no. 1, pp. 25–31.
  29. K. Ikawa, F. Takami, Y. Fukui, and K. Tokuyama, “A novel reagent for the vilsmeier-haack reaction,” Tetrahedron Letters, vol. 10, no. 38, pp. 3279–3281, 1969. View at Google Scholar · View at Scopus
  30. W. S. El-Hamouly, K. M. Amin, S. A. El-Assaly, and E. A. A. El-Meguid, “Synthesis and antitumor activity of some new N-substituted-sulfonyl, 1,2,4-triazole, N-substituted-benzylidene and pyrrole derivatives attached to 4-(benzo[d]thiazol-2-yl)benzohydrazide,” Der Pharma Chemica, vol. 3, no. 6, pp. 293–306, 2011. View at Google Scholar · View at Scopus
  31. P. Skehan, R. Storeng, D. Scudiero et al., “New colorimetric cytotoxicity assay for anticancer-drug screening,” Journal of the National Cancer Institute, vol. 82, no. 13, pp. 1107–1112, 1990. View at Google Scholar · View at Scopus