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Journal of Chemistry
Volume 2014, Article ID 430573, 14 pages
http://dx.doi.org/10.1155/2014/430573
Research Article

Fluorine Substituted 1,2,4-Triazinones as Potential Anti-HIV-1 and CDK2 Inhibitors

Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia

Received 16 February 2014; Accepted 25 April 2014; Published 21 May 2014

Academic Editor: Stojan Stavber

Copyright © 2014 Mohammed S. I. Makki 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. E. De Clercq, “New developments in anti-HIV chemotherapy,” Biochimica et Biophysica Acta, Molecular Basis of Disease, vol. 1587, no. 2-3, pp. 258–275, 2002. View at Publisher · View at Google Scholar · View at Scopus
  2. E. De Clercq, “Antiviral drugs in current clinical use,” Journal of Clinical Virology, vol. 30, no. 2, pp. 115–133, 2004. View at Publisher · View at Google Scholar · View at Scopus
  3. C. M. Kitchen, S. G. Kitchen, J. A. Dubin, and M. S. Gottlieb, “Initial virological and immunologic response to highly active antiretroviral therapy predicts long-term clinical outcome,” Clinical Infectious Diseases, vol. 33, no. 4, pp. 466–472, 2001. View at Publisher · View at Google Scholar · View at Scopus
  4. W. M. Valenti, “HAART is cost-effective and improves outcomes,” AIDS Reader, vol. 11, no. 5, pp. 260–262, 2001. View at Google Scholar · View at Scopus
  5. J. T. King Jr., A. C. Justice, M. S. Roberts, C.-C. H. Chang, and J. S. Fusco, “Long-term HIV/AIDS survival estimation in the highly active antiretroviral therapy era,” Medical Decision Making, vol. 23, no. 1, pp. 9–20, 2003. View at Publisher · View at Google Scholar · View at Scopus
  6. A. Carr, “Toxicity of antiretroviral therapy and implications for drug development,” Nature Reviews Drug Discovery, vol. 2, no. 8, pp. 624–634, 2003. View at Google Scholar · View at Scopus
  7. J. Martinez-Picado, M. P. DePasquale, N. Kartsonis et al., “Antiretroviral resistance during successful therapy of HIV type 1 infection,” Proceedings of the National Academy of Sciences of the United States of America, vol. 97, no. 20, pp. 10948–10953, 2000. View at Google Scholar · View at Scopus
  8. S. J. Little, S. Holte, J.-P. Routy et al., “Antiretroviral-drug resistance among patients recently infected with HIV,” The New England Journal of Medicine, vol. 347, no. 6, pp. 385–394, 2002. View at Publisher · View at Google Scholar · View at Scopus
  9. E. Pomarnacka and A. Kornicka, “Synthesis and in vitro anticancer and anti-HIV evaluation of new 2-mercaptobenzenesulfonamides,” Farmaco, vol. 56, no. 8, pp. 571–577, 2001. View at Publisher · View at Google Scholar · View at Scopus
  10. D. A. Karnofsky, “Mechnaism of action of anticancer drugs at a cellular level,” Ca-A Cancer Journal for Clinicians, vol. 18, no. 4, pp. 232–234, 1968. View at Google Scholar · View at Scopus
  11. S. T. M. Makki, D. A. Bakhotmah, R. M. Abdel-Rahman, and M. S. El-Shahawy, “Designing and synthesis of new fluorine substituted pyrimidine-thion-5-carbonitriles and the related derivatives as photochemical probe agents for inhibition of vitiligo disease,” International Journal of Organic Chemistry, vol. 2, no. 3, pp. 311–320, 2012. View at Publisher · View at Google Scholar
  12. R. M. Abdel-Rahman, M. S. I. T. Makki, and W. A. Bawazir, “Synthesis of some more fluorine heterocyclic nitrogen systems derived from sulfa drugs as photochemical probe agents for inhibition of vitiligo disease-part i,” E-Journal of Chemistry, vol. 8, no. 1, pp. 405–414, 2011. View at Google Scholar · View at Scopus
  13. R. M. Abdel-Rahman, M. S. I. T. Makki, and W. A. B. Bawazir, “Synthesis of fluorine heterocyclic nitrogen systems derived from sulfa drugs as photochemical probe agents for inhibition of vitiligo disease-Part II,” E-Journal of Chemistry, vol. 7, no. 1, pp. S93–S102, 2010. View at Google Scholar · View at Scopus
  14. D.-J. Wang, L. Fan, C.-Y. Zheng, and Z.-D. Fang, “Synthesis and anti-microbial activity of some new fluorinated 1H-pyrazoles,” Journal of Fluorine Chemistry, vol. 131, no. 5, pp. 584–586, 2010. View at Publisher · View at Google Scholar · View at Scopus
  15. R. Filler and R. Saha, “Fluorine in medicinal chemistry: a century of progress and a 60-year retrospective of selected highlights,” Future Medicinal Chemistry, vol. 1, no. 5, pp. 777–791, 2009. View at Publisher · View at Google Scholar · View at Scopus
  16. G. Sandford, “Elemental fluorine in organic chemistry (1997–2006),” Journal of Fluorine Chemistry, vol. 128, no. 2, pp. 90–104, 2007. View at Publisher · View at Google Scholar · View at Scopus
  17. C. Isanbor and D. O'Hagan, “Fluorine in medicinal chemistry: a review of anti-cancer agents,” Journal of Fluorine Chemistry, vol. 127, no. 3, pp. 303–319, 2006. View at Publisher · View at Google Scholar · View at Scopus
  18. B. E. Smart, “Fluorine substituent effects (on bioactivity),” Journal of Fluorine Chemistry, vol. 109, no. 1, pp. 3–11, 2001. View at Publisher · View at Google Scholar · View at Scopus
  19. S. Liu, X. Qian, G. Song, J. Chen, and W. Chen, “Fluorine containing heterocyclic compounds: Synthesis of 6-substituted-2-substituted-aryl-1,2,4-triazolo[5,1-b] 1,3,5-thiadiazin-7-one derivatives,” Journal of Fluorine Chemistry, vol. 105, no. 1, pp. 111–115, 2000. View at Google Scholar · View at Scopus
  20. R. M. Abdel-Rahman, “Synthesis and chemistry of fluorine containing bioactive 1,2,4-triazines—an overview: chemistry of uncondensed 1,2,4-triazines, part III,” Pharmazie, vol. 54, no. 11, pp. 791–803, 1999. View at Google Scholar · View at Scopus
  21. T. . Ramadan, R. M. Abdel-Rahman, and M. Seada, “Studies on complexes of Cu(II), Ni(II), Co(II) and Ln(II) with 3-(α-benzoyl)benzylidene hydrazino-5,6-diphenyl-1,2,4-triazine,” Asian Journal of Chemistry, vol. 4, pp. 569–575, 1992. View at Google Scholar
  22. A. A. T. Ramadan, R. M. Abdel-Rahman, M. A. El-Behairy, A. I. Ismail, and M. M. Mahmoud, “The thermodynamics of complexation of transition and lanthanide ions by 3-(α-carboxymethylaminobenzyli-denehydrazino)-5,6-diphenyl-1,2,4 triazine (HipHt),” Thermochimica Acta, vol. 222, no. 2, pp. 291–303, 1993. View at Google Scholar · View at Scopus
  23. F. M. Foss, “Nucleoside analogs and antimetabolite therapies for myelodysplastic syndrome,” Best Practice and Research: Clinical Haematology, vol. 17, no. 4, pp. 573–584, 2004. View at Publisher · View at Google Scholar · View at Scopus
  24. G. S. Cockerill and K. E. Lackey, “Small molecule inhibitors of the class 1 receptor tyrosine kinase family,” Current topics in medicinal chemistry, vol. 2, no. 9, pp. 1001–1010, 2002. View at Google Scholar · View at Scopus
  25. E. K. Rowinsky, “Signal Events: cell Signal Transduction and Its Inhibition in Cancer,” Oncologist, vol. 8, no. 3, pp. 5–17, 2003. View at Google Scholar · View at Scopus
  26. V. Aparna, G. Rambabu, S. K. Panigrahi, J. A. R. P. Sarma, and G. R. Desiraju, “Virtual screening of 4-anilinoquinazoline analogues as EGFR kinase inhibitors: importance of hydrogen bonds in the evaluation of poses and scoring functions,” Journal of Chemical Information and Modeling, vol. 45, no. 3, pp. 725–738, 2005. View at Publisher · View at Google Scholar · View at Scopus
  27. S. Emanuel, R. H. Gruninger, A. Fuentes-Pesquera et al., “A vascular endothelial growth factor receptor-2 kinase inhibitor potentiates the activity of the conventional chemotherapeutic agents paclitaxel and doxorubicin in tumor xenograft models,” Molecular Pharmacology, vol. 66, no. 3, pp. 635–647, 2004. View at Publisher · View at Google Scholar · View at Scopus
  28. R. M. Abdel-Rahman, “Role of uncondensed 1,2,4-triazine compounds and related heterobicyclic systems as therapeutic agents—a review,” Pharmazie, vol. 56, no. 1, pp. 18–22, 2001. View at Google Scholar · View at Scopus
  29. R. M. Abdel-Rahman, “Synthesis and anti human immune virus activity of some new fluorine containing substituted-3-thioxo-1,2,4-triazin-5-ones,” Farmaco, vol. 46, no. 2, pp. 379–389, 1991. View at Google Scholar · View at Scopus
  30. R. M. Abdel-Rahman, “Synthesis of some new fluorine bearing trisubstituted 3-thioxo-1,2,4- triazin-5-ones as potential anticancer agents,” Farmaco, vol. 47, no. 3, pp. 319–326, 1992. View at Google Scholar · View at Scopus
  31. R. M. Abdel-Rahman, M. Seada, M. Fawzy, and I. El-Baz, “Synthesis of some new thioethers of 1,2,4-triazine-3-hydrazones and assays for their anticancer and anti human immune virus activities,” Farmaco, vol. 48, no. 3, pp. 397–406, 1993. View at Google Scholar · View at Scopus
  32. R. M. Abdel-Rahman, M. Seada, M. Fawzy, and I. El-Baz, “Synthesis of some new 1,6-dihydro-3-substituted 6-spiro-(9'-fluorene)-1,2,4-triazin-5-(4H)-ones as potential anti HIV and anticancer drugs,” Pharmazie, vol. 49, no. 10, pp. 729–733, 1994. View at Google Scholar · View at Scopus
  33. R. M. Abdel-Rahman, M. Seada, M. Fawzy, and I. El-Baz, “Synthesis of some new heterobicyclic compounds containing spiro-1,2,4-triazine moiety as potential anti-HIV and anticancer agents,” Pharmazie, vol. 49, no. 11, pp. 811–814, 1994. View at Google Scholar · View at Scopus
  34. A. M. Abdel-Halim, Z. El-Gendy, and R. M. Abdel-Rahman, “Synthesis and biological activity of 1,2,4-triazinotriazinone derivatives,” Pharmazie, vol. 50, no. 11, pp. 726–729, 1995. View at Google Scholar · View at Scopus
  35. R. M. Abdel-Rahman, J. M. Morsy, F. Hanafy, and H. A. Amene, “Synthesis of heterobicyclic nitrogen systems bearing the 1,2,4-triazine moiety as anti-HIV and anticancer drugs: part I,” Pharmazie, vol. 54, no. 5, pp. 347–351, 1999. View at Google Scholar · View at Scopus
  36. R. M. Abdel-Rahman, J. M. Morsy, S. El-Edfawy, and H. A. Amine, “Synthesis of some new heterobicyclic nitrogen systems bearing the 1,2,4- triazine moiety as anti-HIV and anti-cancer drugs, part II,” Pharmazie, vol. 54, no. 9, pp. 667–671, 1999. View at Google Scholar · View at Scopus
  37. Z. El-Gendy, J. M. Morsy, H. A. Allimony, W. R. Abdel-Monem Ali, and R. M. Abdel-Rahman, “Synthesis of heterobicyclic nitrogen systems bearing the 1,2,4-triazine moiety as anti-HIV and anticancer drugs, part III,” Pharmazie, vol. 56, no. 5, pp. 376–383, 2001. View at Google Scholar · View at Scopus
  38. Z. El-Gendy, J. M. Morsy, H. A. Allimony, W. R. Abdel-Monem, and R. M. Abdel-Rahman, “Synthesis of heterobicyclic nitrogen systems bearing a 1,2,4-triazine moiety as anticancer drugs: part IV,” Phosphorus, Sulfur and Silicon and the Related Elements, vol. 178, no. 9, pp. 2055–2071, 2003. View at Google Scholar · View at Scopus
  39. V. Kryštof, P. Cankař, I. Fryšová et al., “4-Arylazo-3,5-diamino-1H-pyrazole CDK inhibitors: SAR study, crystal structure in complex with CDK2, selectivity, and cellular effects,” Journal of Medicinal Chemistry, vol. 49, no. 22, pp. 6500–6509, 2006. View at Publisher · View at Google Scholar · View at Scopus
  40. R. M. Abdel-Rahman, “Chemistry of uncondensed 1,2,4-triazines, part iv synthesis and chemistry of bioactive 3-amino-1,2,4-triazines and related compounds—an overview,” Pharmazie, vol. 56, no. 4, pp. 275–286, 2001. View at Google Scholar · View at Scopus
  41. K. F. Khaled, “Adsorption and inhibitive properties of a new synthesized guanidine derivative on corrosion of copper in 0.5 M H2SO4,” Applied Surface Science, vol. 255, no. 5, pp. 1811–1818, 2008. View at Publisher · View at Google Scholar · View at Scopus
  42. T. Gucký, E. Řezníčková, P. Džubák, M. Hajdúch, and V. Kryštof, “Synthesis and anticancer activity of some 1,5-diaryl-3-(3,4,5- Džubák trihydroxyphenyl)-1H-pyrazolo[4,3-e][1,2,4]triazines,” Monatshefte fur Chemie, vol. 141, no. 6, pp. 709–714, 2010. View at Publisher · View at Google Scholar · View at Scopus