Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2014, Article ID 457430, 8 pages
http://dx.doi.org/10.1155/2014/457430
Research Article

Synthesis, Single Crystal X-Ray Structure, and Antimicrobial Activity of 6-(1,3-Benzodioxol-5-ylmethyl)-5-ethyl-2-{[2-(morpholin-4-yl)ethyl]sulfanyl}pyrimidin-4(3H)-one

1Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
2Pharmaceutical and Drug Industries Research Division, Medicinal and Pharmaceutical Chemistry Department, National Research Centre, Dokki, Giza 12622, Egypt
3Department of Chemistry, Faculty of Science, Tanta University, Tanta 31527, Egypt
4Genetic Engineering and Biotechnology Division, Microbial Chemistry Department, National Research Centre, Dokki, Giza 12622, Egypt

Received 8 April 2014; Accepted 8 May 2014; Published 26 May 2014

Academic Editor: Hakan Arslan

Copyright © 2014 Mohamed I. Attia 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. El-Bendary and F. Badria, “Synthesis, DNA-binding, and antiviral activity of certain pyrazolo[3, 4-d]pyrimidine derivatives,” Archiv der Pharmazie, vol. 333, no. 4, pp. 99–103, 2000. View at Google Scholar
  2. J.-H. Chern, K.-S. Shia, T.-A. Hsu et al., “Design, synthesis, and structure-activity relationships of pyrazolo[3,4- d]pyrimidines: a novel class of potent enterovirus inhibitors,” Bioorganic & Medicinal Chemistry Letters, vol. 14, no. 10, pp. 2519–2525, 2004. View at Publisher · View at Google Scholar · View at Scopus
  3. M. S. Novikov, V. T. Valuev-Elliston, D. A. Babkov et al., “N1, N3-disubstituted uracils as nonnucleoside inhibitors of HIV-1 reverse transcriptase,” Bioorganic & Medicinal Chemistry Letters, vol. 21, no. 5, pp. 1150–1158, 2013. View at Publisher · View at Google Scholar
  4. A. Ali, G. E. Taylor, K. Ellsworth et al., “Novel pyrazolo[3,4-d]pyrimidine-based inhibitors of Staphlococcus aureus DNA polymerase III: design, synthesis, and biological evaluation,” Journal of Medicinal Chemistry, vol. 46, no. 10, pp. 1824–1830, 2003. View at Publisher · View at Google Scholar · View at Scopus
  5. A. Trivedi, D. Dodiya, J. Surani et al., “Facile one-pot synthesis and antimycobacterial evaluation of pyrazolo[3,4-d]pyrimidines,” Archiv der Pharmazie, vol. 341, no. 7, pp. 435–439, 2008. View at Publisher · View at Google Scholar · View at Scopus
  6. M. Bakavoli, G. Bagherzadeh, M. Vaseghifar et al., “Molecular iodine promoted synthesis of new pyrazolo[3,4-d]pyrimidine derivatives as potential antibacterial agents,” European Journal of Medicinal Chemistry, vol. 45, no. 2, pp. 647–650, 2010. View at Publisher · View at Google Scholar · View at Scopus
  7. D. Ranganath, A. Mazumdar, S. Mulukuri, R. Doonaboina, M. Devarakonda, and M. R. Prasad, “A novel and eco-friendly procedure for the synthesis of some pyrazolo-thiadiazolo-pyrimidinones and its in vitro anti-bacterial activity,” Medicinal Chemistry Research, vol. 21, no. 9, pp. 2458–2464, 2012. View at Publisher · View at Google Scholar
  8. O. A. Al-Deeb, A. A. Al-Turkistani, E. S. Al-Abdullah, N. R. El-Brollosy, E. E. Habib, and A. A. El-Emam, “Pyrimidine-5-carbonitriles-part III: synthesis and antimicrobial activity of novel 6-(2-substituted propyl)-2, 4-disubstituted pyrimidine-5-carbonitriles,” Heterocyclic Communications, vol. 19, no. 6, pp. 411–419, 2013. View at Google Scholar
  9. A. Angelucci, S. Schenone, G. L. Gravina et al., “Pyrazolo[3,4-d]pyrimidines c-Src inhibitors reduce epidermal growth factor-induced migration in prostate cancer cells,” European Journal of Cancer, vol. 42, no. 16, pp. 2838–2845, 2006. View at Publisher · View at Google Scholar · View at Scopus
  10. F. Manetti, A. Santucci, G. A. Locatelli et al., “Identification of a novel pyrazolo[3,4-d]pyrimidine able to inhibit cell proliferation of a human osteogenic sarcoma in vitro and in a xenograft model in mice,” Journal of Medicinal Chemistry, vol. 50, no. 23, pp. 5579–5588, 2007. View at Publisher · View at Google Scholar · View at Scopus
  11. A. Lauria, I. Abbate, C. Patella, A. Martorana, G. Dattolo, and A. M. Almerico, “New annelated thieno[2, 3-e][1, 2, 3]triazolo[1, 5-a]pyrimidines, with potent anticancer activity, designed though VLAK protocol,” European Journal of Medicinal Chemistry, vol. 62, pp. 416–424, 2013. View at Publisher · View at Google Scholar
  12. M. Amir, S. Javed, and H. Kumar, “Pyrimidine as antiinflammatory agent: a review,” Indian Journal of Pharmaceutical Sciences, vol. 69, no. 3, pp. 337–343, 2007. View at Google Scholar · View at Scopus
  13. A. P. Keche, G. D. Hatnapure, R. H. Tale, A. H. Rodge, S. S. Birajdar, and V. M. Kamble, “A novel pyrimidine derivatives with aryl urea, thiourea and sulfonamide moieties: synthesis, anti-inflammatory and antimicrobial evaluation,” Bioorganic & Medicinal Chemistry Letters, vol. 22, no. 10, pp. 3445–3448, 2012. View at Publisher · View at Google Scholar · View at Scopus
  14. D. J. Nelson, S. W. LaFon, J. V. Tuttle et al., “Allopurinol ribonucleoside as an antileishmanial agent. Biological effects, metabolism, and enzymatic phosphorylation,” The Journal of Biological Chemistry, vol. 254, no. 22, pp. 11544–11549, 1979. View at Google Scholar · View at Scopus
  15. J. J. Marr, R. L. Berens, D. J. Nelson et al., “Antileishmanial action of 4-thiopyrazolo(3,4-d)pyrimidine and its ribonucleoside. Biological effects and metabolism,” Biochemical Pharmacology, vol. 31, no. 2, pp. 143–148, 1982. View at Google Scholar · View at Scopus
  16. S. Guccione, M. Modica, J. Longmore et al., “Synthesis and NK-2 antagonist effect of 1, 6-diphenyl-pyrazolo[3, 4-d]thiazolo[3, 2-a]-4H-pyrimidin-4-one,” Bioorganic & Medicinal Chemistry Letters, vol. 6, no. 1, pp. 59–64, 1996. View at Google Scholar
  17. H. S. Ahn, A. Bercovici, G. Boykow et al., “Potent tetracyclic guanine inhibitors of PDE1 and PDE5 cyclic guanosine monophosphate phosphodiesterases with oral antihypertensive activity,” Journal of Medicinal Chemistry, vol. 40, no. 14, pp. 2196–2210, 1997. View at Publisher · View at Google Scholar
  18. M. Himaja, K. Vandana, A. Ranjitha, M. Ramana, and A. Karigar, “Synthesis, docking studies and antioxidant activity of 1, 3-benzodioxole-5-carboxyl amino acids and dipeptides,” International Research Journal of Pharmacy, vol. 2, no. 6, pp. 57–61, 2011. View at Google Scholar
  19. R. Joshi, M. S. Kumar, K. Satyamoorthy, M. K. Unnikrisnan, and T. Mukherjee, “Free radical reactions and antioxidant activities of sesamol: pulse radiolytic and biochemical studies,” Journal of Agricultural and Food Chemistry, vol. 53, no. 7, pp. 2696–2703, 2005. View at Publisher · View at Google Scholar · View at Scopus
  20. N. Micale, M. Zappalà, and S. Grasso, “Synthesis and cytotoxic activity of 1,3-benzodioxole derivatives. Note II,” Il Farmaco, vol. 58, no. 5, pp. 351–355, 2003. View at Publisher · View at Google Scholar · View at Scopus
  21. A. C. L. Leite, K. P. da Silva, I. A. de Souza, J. M. de Araújo, and D. J. Brondani, “Synthesis, antitumour and antimicrobial activities of new peptidyl derivatives containing the 1,3-benzodioxole system,” European Journal of Medicinal Chemistry, vol. 39, no. 12, pp. 1059–1065, 2004. View at Publisher · View at Google Scholar · View at Scopus
  22. M. H. Mehmood and A. H. Gilani, “Pharmacological basis for the medicinal use of black pepper and piperine in gastrointestinal disorders,” Journal of Medicinal Food, vol. 13, no. 5, pp. 1086–1096, 2010. View at Publisher · View at Google Scholar · View at Scopus
  23. Y. P. Hwang, H. J. Yun, H. G. Kim et al., “Suppression of phorbol-12-myristate-13-acetate-induced tumor cell invasion by piperine via the inhibition of PKCα/ERK1/2-dependent matrix metalloproteinase-9 expression,” Toxicology Letters, vol. 203, no. 1, pp. 9–19, 2011. View at Publisher · View at Google Scholar · View at Scopus
  24. M. N. Aboul-Enein, A. A. El-Azzouny, M. I. Attia et al., “Design and synthesis of novel stiripentol analogues as potential anticonvulsants,” European Journal of Medicinal Chemistry, vol. 47, no. 1, pp. 360–369, 2012. View at Publisher · View at Google Scholar · View at Scopus
  25. V. Diwan, H. Poudyal, and L. Brown, “Piperine attenuates cardiovascular, liver and metabolic changes in high carbohydrate, high fat-fed rats,” Cell Biochemistry and Biophysics, vol. 67, no. 2, pp. 297–304, 2013. View at Publisher · View at Google Scholar · View at Scopus
  26. S. Li, C. Wang, M. Wang, W. Li, K. Matsumoto, and Y. Tang, “Antidepressant like effects of piperine in chronic mild stress treated mice and its possible mechanisms,” Life Sciences, vol. 80, no. 15, pp. 1373–1381, 2007. View at Publisher · View at Google Scholar · View at Scopus
  27. D. P. Bezerra, F. O. de Castro, A. P. N. Alves et al., “In vitro and in vivo antitumor effect of 5-FU combined with piplartine and piperine,” Journal of Applied Toxicology, vol. 28, no. 2, pp. 156–163, 2008. View at Publisher · View at Google Scholar · View at Scopus
  28. N. Flores, I. A. Jiménez, A. Giménez et al., “Antiparasitic activity of prenylated benzoic acid derivatives from Piper species,” Phytochemistry, vol. 70, no. 5, pp. 621–627, 2009. View at Publisher · View at Google Scholar · View at Scopus
  29. F. Cotinguiba, L. O. Regasini, V. da Silva Bolzani et al., “Piperamides and their derivatives as potential anti-trypanosomal agents,” Medicinal Chemistry Research, vol. 18, no. 9, pp. 703–711, 2009. View at Publisher · View at Google Scholar · View at Scopus
  30. M. I. Attia, A. A. El-Emam, A. A. Al-Turkistani, A. L. Kansoh, and N. R. El-Brollosy, “Synthesis of novel 2-(substituted amino)alkylthiopyrimidin-4(3H)-ones as potential antimicrobial agents,” Molecules, vol. 19, no. 1, pp. 279–290, 2014. View at Google Scholar
  31. L. Feng, K. Lv, M. Liu et al., “Synthesis and in vitro antibacterial activity of gemifloxacin derivatives containing a substituted benzyloxime moiety,” European Journal of Medicinal Chemistry, vol. 55, pp. 125–136, 2012. View at Publisher · View at Google Scholar
  32. W. Cunico, C. R. Gomes, M. Moreth et al., “Synthesis and antimalarial activity of hydroxyethylpiperazine derivatives,” European Journal of Medicinal Chemistry, vol. 44, no. 3, pp. 1363–1368, 2009. View at Publisher · View at Google Scholar · View at Scopus
  33. G. Blay, L. Cardona, B. García, L. Lahoz, and J. Pedro, “The reduction of α, β-unsaturated nitriles and α-halonitriles with sodium hydrogen telluride,” Tetrahedron, vol. 52, no. 25, pp. 8611–8618, 1996. View at Google Scholar
  34. Brucker, APEX2, SAINT and SADABS, Brucker AXS, Madison, Wis, USA, 2009.
  35. G. M. Sheldrick, “A short history of SHELX,” Acta Crystallographica A: Foundations of Crystallography, vol. 64, no. 1, pp. 112–122, 2008. View at Publisher · View at Google Scholar · View at Scopus
  36. C. Penna, S. Marino, G. Gutkind, M. Clavin, G. Ferraro, and V. Martino, “Antimicrobial activity of Eupatorium species growing in Argentina,” Journal of Herbs, Spices & Medicinal Plants, vol. 5, no. 2, pp. 21–28, 1998. View at Google Scholar
  37. T. D. Wikins, L. V. Holdeman, I. J. Abramson, and W. Moore, “Standardized single-disc method for antibiotic susceptibility testing of anaerobic bacteria,” Antimicrobial Agents and Chemotherapy, vol. 1, no. 6, pp. 451–459, 1972. View at Google Scholar · View at Scopus
  38. A. Fürstner, “Recent advancements in the Reformatsky reaction,” Synthesis, no. 8, pp. 571–590, 1989. View at Google Scholar