Advertisement

Russian Journal of General Chemistry

, Volume 86, Issue 12, pp 2865–2869 | Cite as

Conventional and microwave-assisted synthesis of quinolone carboxylic acid derivatives

  • Y. MirzaieEmail author
  • J. Lari
  • H. Vahedi
  • M. Hakimi
Article
  • 111 Downloads

Abstract

Various antibacterial fluoroquinolone compounds are synthesized by the direct amination of 7-halo-6-fluoroquinolone-3-carboxylic acids with a variety of piperazine derivatives and (4aR,7aR)-octahydro-1H-pyrrolo[3,4-b]pyridine using microwave under different reaction conditions. Solvent free high yield microwave synthesis of antibacterial fluoroquinolone compounds is convenient, rapid and environmentally friendly method.

Keywords

synthesis rapid amination antibacterial fluoroquinolone compounds microwave irradiation solvent free reaction enrofloxacin 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Fernandes, P.B., Shipkowitz, N., Bower, R.R., Jarvis, K.P., Weisz, J., and Chu, D.T., J. Antimicrob. Chemother., 1986, vol. 18, no. 6, p. 693. doi 10.1093/jac/18.6.693CrossRefGoogle Scholar
  2. 2.
    Stein, G.E. and Goldstein, E.J., Clin. Infect. Dis., 2006, vol. 42, no. 11, p. 1598. doi 10.1086/503907CrossRefGoogle Scholar
  3. 3.
    Llorente, B., Leclerc, F., and Cedergren, R., Bioorg. Med. Chem., 1996, vol. 4, no. 1, p. 61. doi 10.1016/0968-0896(96)83749-7CrossRefGoogle Scholar
  4. 4.
    Wentland, M.P., Lesher, G.Y., Reuman, M., Gruett, M.D., Singh, B., Aldous, S.C., Dorff, P.H., Rake, J.B., and Coughlin, S.A., J. Med. Chem., 1993, vol. 36, no. 19, p. 2801. doi 10.1021/jm00071a010CrossRefGoogle Scholar
  5. 5.
    Elsea, S.H., Osheroff, N., and Nitiss, J.L., J. Biol. Chem., 1992, vol. 267, no. 19, p. 13150.PubMedGoogle Scholar
  6. 6.
    Oh, Y.S., Lee, C.W., Chung, Y.H., Yoon, S.J., and Cho, S.H., J. Heterocycl. Chem., 1998, vol. 35, no. 3, p. 541. doi 10.1002/jhet.5570350309CrossRefGoogle Scholar
  7. 7.
    Karlowsky, J.A., Adam, H.J., Desjardins, M., Lagacé-Wiens, P.R., Hoban, D.J., Zhanel, G.G., Baxter, M.R., Nichol, K.A., Walkty, A., and Alliance, C.A.R., J. Antimicrob. Chemother., 2013, vol. 68, no. supp. 1, p. i39. doi 10.1093/jac/dkt025CrossRefGoogle Scholar
  8. 8.
    Gootz, T.D. and Brighty, K.E., Med. Res. Rev., 1996, vol. 16, no. 5, p. 433. doi 10.1002/(SICI)1098-1128 (199609)16:5<433::AID-MED3>3.0.CO;2-WCrossRefGoogle Scholar
  9. 9.
    Aubry, A., Pan, X.-S., Fisher, L.M., Jarlier, V., and Cambau, E., Antimicrob. Agents Chemother., 2004, vol. 48, no. 4, p. 1281. doi 10.1128/AAC.48.4.1281-1288.2004CrossRefGoogle Scholar
  10. 10.
    Mitscher, L.A., Chem. Rev., 2005, vol. 105, no. 2, p. 559. doi 10.1021/cr030101qCrossRefGoogle Scholar
  11. 11.
    Sriram, D., Aubry, A., Yogeeswari, P., and Fisher, L., Bioorg. Med. Chem. Lett., 2006, vol. 16, no. 11, p. 2982. doi 10.1016/j.bmcl.2006.02.065CrossRefGoogle Scholar
  12. 12.
    Dubar, F., Anquetin, G., Pradines, B., Dive, D., Khalife, J., and Biot, C., J. Med. Chem., 2009, vol. 52, no. 24, p. 7954. doi 10.1021/jm901357nCrossRefGoogle Scholar
  13. 13.
    Shindikar, A.V. and Viswanathan, C., Bioorg. Med. Chem. Lett., 2005, vol. 15, no. 7, p. 1803. doi 10.1016/j.bmcl.2005.02.037CrossRefGoogle Scholar
  14. 14.
    Grohe, K. and Heitzer, H., Liebigs Annalen der Chemie, 1987, vol. 1987, no. 1, p. 29. doi 10.1002/jlac.198719870106CrossRefGoogle Scholar
  15. 15.
    Petersen, U., Grohe, K., and Kuck, K.H., U.S. Patent 4563459, 1986.Google Scholar
  16. 16.
    Petersen, U., Schrock, W., Habich, D., Krebs, A., Schenke, T., Philipps, T., Grohe, K., Endermann, R., Bremm, K.-D., and Metzger, K.-G., U.S. Patent 5480879, 1996.Google Scholar
  17. 17.
    Van, Z.W.J., Marx, A.F., Koger, H.S., and Booy, J., European Patent 0368410, 1990.Google Scholar
  18. 18.
    Hayakawa, I., Atarashi, S., Imamura, M., Yokohama, S., Higashihashi, N., Sakano, K., and Ohshima, M., U.S. Patent 4985557, 1991.Google Scholar
  19. 19.
    Hayakawa, I., Hiramitsu, T., and Tanaka, Y., Chem. Pharm. Bull., 1984, vol. 32, no. 12, p. 4907. doi 10.1248/cpb.32.4907CrossRefGoogle Scholar
  20. 20.
    Tuberculosis, 2008, vol. 88, no. 2, p. 127. doi 10.1016/S1472-9792(08)70016-7.Google Scholar
  21. 21.
    Guruswamy, B. and Arul, R., Lett. Drug Design & Discovery, 2013, vol. 10, no. 1, p. 86. doi 10.2174/157018013804142492CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2016

Authors and Affiliations

  1. 1.Department of ChemistryPayame Noor University (PNU)TehranIran

Personalised recommendations