Advertisement

Russian Journal of Bioorganic Chemistry

, Volume 40, Issue 1, pp 106–113 | Cite as

Site selectivity in reactions of hydrazonoyl halides with heterocycles containing amino and thione groups leading to fused heterocycles of potential antimicrobial activity

  • M. E. A. Khalifa
  • M. A. Amin
  • M. A. N. MosselhiEmail author
Article

Abstract

Reaction of hydrazonoyl halides with 6-(benzylidenamino)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one and 2,3-diaminoquinazolin-4-one site-selectively afforded 3-substituted-7-(benzylidenamino)-1-phenyl-[1,2,4]triazolo[4,3-a]-pyrimidin-5(1H)-ones, [1,2,4,5]tetrazino[6,1-b]quinazolin-6(4H)-one, and 3-methyl-2-(4-substituted-phenylhydrazo)-[1,2,4]triazino[3,2-b]quinazolin-10-ones in good yields. The structures of the newly synthesized compounds were elucidated by chemical evidence and their IR, 1H, 13C NMR, and MS spectra. Furthermore, some of the products were screened against different strains of bacteria and fungi.

Keywords

hydrazonoyl halide site-selectivity quinazoline pyrimidine antimicrobial activity 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Abbass, I.M., Abdallah, M.A., Mosselhi, M.A.N., Mohammed, S.Z., and Shawali, A.S., J. Chem. Res., 1994, vol. S, pp. 308–309.Google Scholar
  2. 2.
    Albar, H.A., Abdalha, M.A., Mosselhi, M.A.N., and Shawali, A.S., Heteroatom Chem., 1996, vol. 7, pp. 225–228.CrossRefGoogle Scholar
  3. 3.
    Shawali, A.S., Mosselhi, M.A.N, and Tawfik, N.M.A., J. Org. Chem., 2001, vol. 66, pp. 4055–4057.PubMedCrossRefGoogle Scholar
  4. 4.
    Shawali, A.S., Abdalha, M.A., Mosselhi, M.A.N., and Farghaly, T.A.A., Heteroatom Chem., 2002, vol. 13, pp. 136–140.CrossRefGoogle Scholar
  5. 5.
    Shawali, A.S. and Samy, N.A., Open Bioactive Comp. J., 2009, vol. 2, pp. 8–16.CrossRefGoogle Scholar
  6. 6.
    Abdel Hafez, N.A., Farghaly, T.A., Al-Omar, M.A., and Abdalla, M.M., Eur. J. Med. Chem., 2010, vol. 45, pp. 4838–4844.PubMedCrossRefGoogle Scholar
  7. 7.
    Farghaly, T.A., Abbas, I.M., Abdalla, M.M., and Mahgoub, R.O.A., Arkivoc, 2012, vol. vi., pp. 57–70.CrossRefGoogle Scholar
  8. 8.
    Farghaly, T.A, Gomha, S.M., Abbas, E.M.H., and Abdalla, M.M., Arch. Pharm. Chem. Life Sci., 2012, vol. 345, pp. 117–122.CrossRefGoogle Scholar
  9. 9.
    Abdelhamid, A.O., Fahmi, A.A., and Halim, K.N.M., Eur. J. Chem., 2011, vol. 2, pp. 317–323.CrossRefGoogle Scholar
  10. 10.
    Shawali, A.S. and Edrees, M.M., Arkivoc, 2006, vol. IX, pp. 292–365.Google Scholar
  11. 11.
    Mosselhi, M.A.N., Monatsh. Chem. (Chem. Month.), 2002, vol. 133, pp. 1297–1304.CrossRefGoogle Scholar
  12. 12.
    Shawali, A.S., Mosselhi, M.A.N., and Farghaly T.A., Sulfur Silicon Relat. Elem., 2005, vol. 180, pp. 2391–2402.CrossRefGoogle Scholar
  13. 13.
    Shawali, A.S., Mosselhi, M.A.N, and Hussein, A.M., J. Sulfur Chem., 2006, vol. 27, pp. 329–339.CrossRefGoogle Scholar
  14. 14.
    Shawali, A.S., Abdallah, M.A., Mosselhi, M.A.N, and Elewa, M.S., J. Heterocycl. Chem., 2007, vol. 44, pp. 1–4.CrossRefGoogle Scholar
  15. 15.
    Shawali, A.S., Mosselhi, M.A.N, Abdallah, M.A, and Elewa, M.S., J. Chem. Res., 2008, vol. 2, pp. 67–69.CrossRefGoogle Scholar
  16. 16.
    Shawali, A.S. and Farghaly, T.A., Arkivoc, 2008, vol. i, pp. 18–64.CrossRefGoogle Scholar
  17. 17.
    Galarcei, G.D., Foncea, R.E., Edwards, A.M., Pessoamahana, H., Mahana, C.D.P., and Ebenspergeri R.A., Biol. Res., 2008, vol. 41, pp. 43–50.Google Scholar
  18. 18.
    Dolzhenko, A.V., Foo, M.C., Tan, B.J., Dolzhenko, A.V., Chiu, G.N.C., and Chui, W.K., Heterocycles, 2009, vol. 78, pp. 1761–1775.CrossRefGoogle Scholar
  19. 19.
    Vostrova, L.N., Voronina, T.A., Karaseva, T.L., Gernega, S.A., Ivanov, E.I., Kirichenko, A.M., and Totrova, Yu.M., Pharma. Chem. J., 1986, vol. 20, pp. 404–406.CrossRefGoogle Scholar
  20. 20.
    Hawkins, M.E., Pfleiderer, W., Jungmann, O., and Balis, F.M., Anal. Biochem., 2001, vol. 298, pp. 231–240.PubMedCrossRefGoogle Scholar
  21. 21.
    Nakamura, M.Y., Fukunaga, Y., Sasa, K., Ohtoshi, Y., Kanaori, K., Hayashi, H., Nakano, H., and Yamana, K., Nucleic Acids Res., 2005, vol. 33, pp. 5887–5895.PubMedCentralPubMedCrossRefGoogle Scholar
  22. 22.
    Luo, H.-Y., Zhang, X.-B., Hea, C.-L., Shen, G.-L., and Yu, R.-Q., Spectrochimica Acta Part A, 2008, vol. 70, pp. 337–342.CrossRefGoogle Scholar
  23. 23.
    Mosselhi, M.A.N. and Break, L.M., Nucl. Nucl. Nucleic Acids, 2011, vol. 30, pp. 681–695.CrossRefGoogle Scholar
  24. 24.
    Ghorab, M.M., Heiba, H.I., Amina. Hassan, A.A., Abd El-Aziz, A.B., and El-Gazzar, M.G., J. Am. Sci., 2011, vol. 7, pp. 1063–1073.Google Scholar
  25. 25.
    Deshmukh, M.B., Salunkhe, S.M., Patil, D.R., and Anbhule, P.V., Eur. J. Med. Chem., 2009, vol. 44, pp. 2651–2654.PubMedCrossRefGoogle Scholar
  26. 26.
    Atul, R.G., Kiran, S.T., Fazal, S., Mukund, V.D., and Kumar, V.S., Tetrahedron, 2008, vol. 64, pp. 10214–10223.CrossRefGoogle Scholar
  27. 27.
    Azas, N., Rathelot, P., Djekou, S., Delmas, F., Gellis, A., Di-Giorgio, C., Vanelle, P., and Timon-David, P., Il Farmaco, 2003, vol. 58, pp. 1263–1270.PubMedCrossRefGoogle Scholar
  28. 28.
    Said, S.A., Amr A.E., Sabry N.M., and Abdalla M.M., Eur. J. Med. Chem., 2009, vol. 44, pp. 4787–4792.PubMedCrossRefGoogle Scholar
  29. 29.
    Ghorab, M.M., Ragab, F.A., Heiba, H.I., Youssef, H.A., and El-Gazzar, M.G., Bioorg. Med. Chem. Lett., 2010, vol. 20, pp. 6316–6320.PubMedCrossRefGoogle Scholar
  30. 30.
    Shawali, A.S., Abdallah, M.A., and Zayed, M.M., J. Heterocycl. Chem., 2002, vol. 39, pp. 45–49.CrossRefGoogle Scholar
  31. 31.
    Shawali, A.S., Hassaneen, H.M., Shetta, A.F, Osman, A., Heterocycles, 1982, vol. 19, pp. 57–62.CrossRefGoogle Scholar
  32. 32.
    Mohamed, N.R., El-Saidi, M.M.T., Ali, Y.M., and Elnagdi, M.H., Bioorg. Med. Chem., 2007, vol. 15, pp. 6227–6235.PubMedCrossRefGoogle Scholar
  33. 33.
    Bowie, R.A., Edwards, P.N., Nicholson, S., Taylor, P.J., and Thomson, D.A., J. Chem. Soc. Perkin Trans., 1979, vol. 2, pp. 1708–1714.CrossRefGoogle Scholar
  34. 34.
    Elliott, A.J., Callaghan, P.D., Gibson, M.S., and Nemeth, S.T., Can. J. Chem., 1975, vol. 53, pp. 1484–1488.CrossRefGoogle Scholar
  35. 35.
    Bauer, A.W., Kirby, W.M., Sherris, C., and Turck, M., Am. J. Clin. Phath., 1966, vol. 45, pp. 493–496.Google Scholar
  36. 36.
    Pfaller, M.A., Burmeister, L., Bartlett, M.A., and Rinaldi, M.G., J. Clin. Microbiol., 1988, vol. 26, pp. 1437–1441.PubMedCentralPubMedGoogle Scholar
  37. 37.
    Matar, M.J., Ostrosky-Zeichner, L., Paetznick, V.L., Rodriguez, J.R., Chen, E., and Rex J.H., Antimicrob. Agents Chemother., 2003, vol. 47, pp. 1647–1651.PubMedCentralPubMedCrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2014

Authors and Affiliations

  • M. E. A. Khalifa
    • 1
  • M. A. Amin
    • 1
    • 2
  • M. A. N. Mosselhi
    • 1
    • 3
    Email author
  1. 1.Department of Chemistry, Faculty of ScienceTaif UniversityTaifSaudi Arabia
  2. 2.Department of Chemistry, Faculty of ScienceSuez Canal UniversityIsmailiaEgypt
  3. 3.Department of Chemistry, Faculty of ScienceCairo UniversityGizaEgypt

Personalised recommendations