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Synthesis and antibacterial activity of N-[2-(2-naphthyl)ethyl]piperazinyl quinolones

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Abstract

A series of N-[2-(2-naphthyl)ethyl]piperazinyl quinolones containing a carbonyl related functional groups (oxo- or oxyimino-) on the ethyl spacer was synthesized and evaluated for antibacterial activity. The synthesis of N-[2-(2-naphthyl)ethyl]piperazinyl quinolones was achieved through the versatile and efficient synthetic route that involved reaction of piperazinyl quinolones with appropriate α-bromoketone or α-bromooxime derivatives. The structures of new compounds were confirmed by elemental analysis, IR and NMR spectra. Antibacterial data indicated that some of the new N-[2-(2-naphthyl)ethyl]piperazinyl quinolones showed good antibacterial activity and modification of the position 8 and N-1 substituent on quinolone ring, and ethyl spacer functionality produced significant changes in activity against Gram-positive and Gram-negative bacteria.

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References

  1. W. Witte, J. Antimicrob. Chemother. 44A (1999) 1.

    Google Scholar 

  2. D.C. Hooper, Lancet Infect. Dis. 2 (2002) 530.

    CAS  Google Scholar 

  3. S. Emami, A. Shafiee, A. Foroumadi, Mini-Rev. Med. Chem. 6 (2006) 375.

    CAS  Google Scholar 

  4. A. De Sarro, G. De Sarro, Curr. Med. Chem. 8 (2001) 371.

    Google Scholar 

  5. D.C. Hooper, Drugs 58 (1999) 7.

    Google Scholar 

  6. A. Foroumadi, S. Ghodsi, S. Emami, S. Najjari, N. Samadi, M.A. Faramarzi, L. Beikmohammadi, F.H. Shirazi, A. Shafiee, Bioorg. Med. Chem. Lett. 16 (2006) 3499.

    CAS  Google Scholar 

  7. A. Foroumadi, N. Mohammadhosseini, S. Emami, B. Letafat, M.A. Faramarzi, N. Samadi, A. Shafiee, Arch. Pharm. 340 (2007) 47.

    CAS  Google Scholar 

  8. B. Letafat, S. Emami, N. Mohammadhosseini, M.A. Faramarzi, N. Samadi, A. Shafiee, A. Foroumadi, Chem. Pharm. Bull. 55 (2007) 894.

    CAS  Google Scholar 

  9. A. Foroumadi, S. Emami, M. Mehni, M.H. Moshafi, A. Shafiee, Bioorg. Med. Chem. Lett. 15 (2005) 4536.

    CAS  Google Scholar 

  10. A. Shafiee, M. Haddad Zahmatkesh, N. Mohammadhosseini, J. Khalafy, S. Emami, M.H. Moshafi, M. Sorkhi, A. Foroumadi, Daru 16 (2008) 189.

    CAS  Google Scholar 

  11. A. Foroumadi, M. Safavi, S. Emami, F. Siavoshi, S. Najjari, F. Safari, A. Shafiee, Med. Chem. 4 (2008) 498.

    CAS  Google Scholar 

  12. S. Jazayeri, M.H. Moshafi, L. Firoozpour, S. Emami, M. Haddad, F. Pahlavanzadeh, M. Esnaashari, A. Shafiee, A. Foroumadi, Eur. J. Med. Chem. 44 (2009) 1205.

    CAS  Google Scholar 

  13. K.A.M. Walker, M.B. Wallach, D.R. Hirschfeld, J. Med. Chem. 24 (1981) 67.

    CAS  Google Scholar 

  14. European Committee for Antimicrobial Susceptibility Testing (EUCAST) of the European Society of Clinical Microbiology and Infectious Diseases (ESCMID). Determination of Minimum Inhibitory Concentrations (MICs) of Antibacterial Agents by Agar Dilution. Clinical Microbiology and Infection, Eucast Definitive Document E. Def 3.1 (2000) 6, pp. 509–515.

    Google Scholar 

  15. S. Emami, A. Shafiee, Heterocycles 55 (2001) 2059.

    CAS  Google Scholar 

  16. S. Emami, M. Falahati, A. Banifatemi, M. Amanlou, A. Shafiee, Bioorg. Med. Chem. 12 (2004) 3971.

    CAS  Google Scholar 

  17. S. Emami, M. Falahati, A. Banifatemi, A. Shafiee, Bioorg. Med. Chem. 12 (2004) 5881.

    CAS  Google Scholar 

  18. H. Baji, M. Flammang, T. kimny, F. Gasquez, P.L. Compagnon, A. Delcourt, Eur. J. Med. Chem. 30 (1995) 617.

    CAS  Google Scholar 

  19. K.-C. Fang, Y.-L. Chen, J.-Y. Sheu, T.-C. Wang, C.-C. Tzeng, J. Med. Chem. 43 (2000) 3809.

    CAS  Google Scholar 

  20. G.E. Hawkes, K. Herwig, J.D. Roberts, J. Org. Chem. 39 (1974) 1017.

    CAS  Google Scholar 

  21. M.S. Gordon, S.A. Sojka, J.G. Krause, J. Org. Chem. 49 (1984) 97.

    CAS  Google Scholar 

  22. B. Letafat, S. Emami, A. Aliabadi, N. Mohammadhosseini, M.H. Moshafi, A. Asadipour, A. Shafiee, A. Foroumadi, Arch. Pharm. 341 (2008) 497.

    CAS  Google Scholar 

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Shafiee, A., Emami, S., Ghodsi, S. et al. Synthesis and antibacterial activity of N-[2-(2-naphthyl)ethyl]piperazinyl quinolones. JICS 6, 325–333 (2009). https://doi.org/10.1007/BF03245841

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  • DOI: https://doi.org/10.1007/BF03245841

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