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Synthesis and antimicrobial activity of some new substituted pyrido[3′,2′:4,5]thieno[3,2-d]-pyrimidinone derivatives

Russian Journal of Bioorganic Chemistry volume 40, pages 308–313 (2014)Cite this article

Abstract

A series of new 3-substituted-7-(2-chloro-6-ethoxypyridin-4-yl)-9-(2,4-dichlorophenyl)-2-methylpyrido[3′,2′:4,5]thieno[3,2-d]pyrimidin-4(3H)-one derivatives were synthesized as antimicrobial agents using 7-(2-chloro-6-ethoxypyridin-4-yl)-9-(2,4-dichlorophenyl)-2-methyl-4H-pyrido[3′,2′:4,5]thieno[3,2-d]-[1,3]oxazin-4-one as a starting compound. Its condensation with substituted aniline derivatives or phenyl hydrazine gave the corresponding N-substituted derivatives. Treatment of the starting compound with hydrazine hydrate afforded the corresponding N-amino derivative, which was reacted with substituted phenylisocyanate and phenylisothiocyanate derivatives to give the corresponding semicarbazides and thiosemicarbazide derivatives. All the newly synthesized compounds were evaluated for their antimicrobial activities in comparison to streptomycin and fusidic acid as positive controls. The structure assignments of the new compounds are based on chemical and spectroscopic evidence.

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References

  1. Hossan, A.S.M., Abu-Melha, H.M.A., Al-Omar, M.A., and Amr, A.E., Molecules, 2012, vol. 17, pp. 13642–13655.

    CAS  PubMed  Article  Google Scholar 

  2. Al-Mohizea, A.M., Al-Omar, M.A., Abdalla, M.M., and Amr, A.E., Int. J. Biol. Macromol., 2012, vol. 50, pp. 171–179.

    CAS  PubMed  Article  Google Scholar 

  3. Khalifa, N.M., Al-Omar, M.A., Amr, A.E., and Haiba, M.E., Int. J. Biol. Macromol., 2013, vol. 54, pp. 51–56.

    CAS  PubMed  Article  Google Scholar 

  4. Al-Harbi, N.O., Bahashwan, S.A., Fayed, A.A., Aboonq, M.S., and Amr, A.E., Int. J. Biol. Macromol., 2013, vol. 57, pp. 165–173.

    CAS  PubMed  Article  Google Scholar 

  5. Bahashwan, S.A., Al-Harbi, N.O., Fayed, A.A., Amr, A.E., Shadid, K.A., Alalawi, A.M., and Bassati, I.M.S., Int. J. Biol. Macromol., 2012, vol. 51, pp. 7–17.

    CAS  PubMed  Article  Google Scholar 

  6. Ouf, N.H. and Amr, A.E., Monatsh. Chem., 2008, vol. 139, pp. 579–585.

    CAS  Article  Google Scholar 

  7. Amr, A.E., Mohamed, A.M., Mohamed, S.F., Abdel-Hafez, N.A., and Hammam, A.G., Bioorg. Med. Chem., 2006, vol. 14, pp. 5481–5488.

    CAS  PubMed  Article  Google Scholar 

  8. Abou-Ghalia M.H., and Amr, A.E., Amino Acids, 2004, vol. 26, pp. 283–289.

    Google Scholar 

  9. Amr, A.E., Hegab, M.I., Ibrahim, A.A., and Abdulla, M.M., Monatsh. Chem., 2003, vol. 134, pp. 1395–1409.

    CAS  Article  Google Scholar 

  10. Chakrabarti, J.K., Horsman, L., Hotten, T.M., Pullar, I.A., Tupper, D.E., and Wright, F.C., J. Med. Chem., 1980, vol. 23, pp. 878–884.

    CAS  PubMed  Article  Google Scholar 

  11. Ram, V.J., Pandey, H.K., and Vlietinck, A.J., J. Heterocycl. Chem., 1981, vol. 18, pp. 1277–1285.

    CAS  Google Scholar 

  12. Fahmy, H.H. and El-Eraqy, W., Arch. Pharm. Res., 2001, vol. 24, pp. 171–178.

    CAS  PubMed  Article  Google Scholar 

  13. DeClercq, E., Anticancer Res., 1986, vol. 6, pp. 549–556.

    CAS  Google Scholar 

  14. DeClercq, E., J. Med. Chem., 1986, vol. 29, pp. 156–162.

    Google Scholar 

  15. Hammam, A.G., Sharaf, M., and Abdel-Hafez, N.A., Ind. J. Chem., 2001, vol. 40B, p. 213.

    CAS  Google Scholar 

  16. Hammam, A.G., Fahmy, A.F.M., Amr, A.E., and Mohamed, A.M., Ind. J. Chem. Sec. B., 2003, vol. 42B, pp. 1985–1993.

    CAS  Google Scholar 

  17. Kumar, K.S., Chamakuri, S., Vishweshwar, P., Iqbal, J., and Pal, M., Tetrahedron Letters, 2010, vol. 51, pp. 3269–3273.

    CAS  Article  Google Scholar 

  18. Ola H.R., Omaima G.S., and Ibrahim M.E., Europ. J. Med. Chem., 2012, vol. 55, pp. 85–93.

    Article  Google Scholar 

  19. Pédeboscq, S., Gravier, D., Casadebaig, F., Hou, G., Gissot, A., De Giorgi, F., Ichas, F., Cambar, J., and Pometan, J., Europ. J. Med. Chem., 2010, vol. 45, pp. 2473–2479.

    Article  Google Scholar 

  20. Ashour, H.M., Shaaban, O.G., Rizk, O.H., and El-Ashmawy, I.M., Europ. J. Med. Chem., 2013, vol. 62, pp. 341–351.

    CAS  Article  Google Scholar 

  21. Furtada, G.L. and Medeiros, A.A., J. Clin. Microbiol., 1980, vol. 12, 550–556.

    Google Scholar 

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Authors and Affiliations

  1. Respiratory Department Applied Organic & Biochemistry Division, College of Medical Rehabilitation Sciences, Taibah University, Al-Madinah Al-Munawara, 3893, Saudi Arabia

    Ahmed A. Fayed

  2. Applied Organic Chemistry Department, National Research Center, Cairo, Dokki, Egypt

    Ahmed A. Fayed & Abd El-Galil E. Amr

  3. Pharmaceutical Chemistry Department, Drug Exploration & Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh, 11451, Saudi Arabia

    Abd El-Galil E. Amr & Mohamed A. Al-Omar

  4. Department of Microbial Chemistry, National Research Center, Cairo, Egypt

    Elsayed E. Mostafa

Authors
  1. Ahmed A. Fayed
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  2. Abd El-Galil E. Amr
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  3. Mohamed A. Al-Omar
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  4. Elsayed E. Mostafa
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Correspondence to Ahmed A. Fayed.

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Fayed, A.A., Amr, A.EG.E., Al-Omar, M.A. et al. Synthesis and antimicrobial activity of some new substituted pyrido[3′,2′:4,5]thieno[3,2-d]-pyrimidinone derivatives. Russ J Bioorg Chem 40, 308–313 (2014). https://doi.org/10.1134/S1068162014030042

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  • DOI: https://doi.org/10.1134/S1068162014030042

Keywords

  • oxazinone
  • thienopyrimidine
  • semi- and thiosemicarbazides
  • antimicrobial agents