Skip to main content
Log in

Quinoline-3-carboxylates as potential antibacterial agents

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

The ethyl-2-chloroquinoline-3-carboxylates, 4, were achieved from o-aminobenzophenones in two steps. i.e. initially, the ethyl-2-oxoquinoline-3-carboxylates, 3, were obtained by base-catalyzed Friedlander condensations of o-aminobenzophenones, 1, and diethylmalonate, 2. The 2-chloroquinoline-3-carboxylates, 4, were then obtained by the reaction with POCl3 in good yields. The chemical structures were confirmed by FTIR, mass and 1H-NMR spectroscopic techniques. All the synthesized compounds were tested for their in vitro antibacterial activity against Bacillus subtilis and Vibrio cholera and found to possess moderate activity.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. R.G. Stein, J.H. Beil, T. Singh, J. Med. Chem. 13, 153 (1970)

    Article  CAS  Google Scholar 

  2. A.A. Joshi, S.S. Narkhede, C.L. Viswanathan, Bioorg. Med. Chem. Lett. 15, 73 (2005)

    Article  CAS  Google Scholar 

  3. Senniappan Thamarai Selvi, Vetrivel Nadaraj, Sellappan Mohan, Raju Sasia, Manoharan Hema, Bioorg. Med. Chem. 14, 3896 (2006)

    Article  Google Scholar 

  4. G. Roma, M.D. Braccio, G. Grossi, F. Mattioli, M. Ghia, Eur. J. Med. Chem. 35, 1021 (2000)

    Article  CAS  Google Scholar 

  5. G.B. Liu, J.L. Xu, C.C. He, G. Chen, Q. Xu, H.X. Xu, J.X. Li, Bioorg. Med. Chem. 17, 5433 (2009)

    Article  CAS  Google Scholar 

  6. Partha Palit, Priyankar Paira, Abhijit Hazra, Sukdeb Banerjee, Asish Das Gupta, Sujata G. Dastidar, Nirup B. Mondal, Eur. J. Med. Chem. 44, 845 (2009)

    Article  Google Scholar 

  7. A. Dlugosz, D. Dus, Farmaco 51, 367 (1996)

    CAS  Google Scholar 

  8. S.S. Palimkar, S.A. Siddiqui, T. Daniel, R.J. Lahoti, K.V. Srinivasan, J. Org. Chem. 68, 9371 (2003)

    Article  CAS  Google Scholar 

  9. R.H.F. Manske, M. Kukla, Org. React. 7, 59 (1953)

    Google Scholar 

  10. F.W. Bergstrom, Chem. Rev. 35, 153 (1944)

    Article  Google Scholar 

  11. C.C. Cheng, S.J. Yan, Org. React. 28, 37 (1982)

    CAS  Google Scholar 

  12. Edward A. Fehnel, J. Org. Chem. 31(9), 2899 (1966)

    Article  CAS  Google Scholar 

  13. Alexandre V. Ivachtchenko, Alexander V. Khvat, Vladimir V. Kobak, Volodymir M. Kysil, Caroline T. Williams, Tetrahedron Lett. 45, 5473 (2004)

    Article  CAS  Google Scholar 

  14. R.H. Reitsema, Chem. Rev. 43, 47 (1948)

    Article  Google Scholar 

  15. F.W. Bergstrom, Chem. Rev. 35, 156 (1944)

    Article  Google Scholar 

  16. E.A. Fehnel, J. Org. Chem. 31, 2899 (1966)

    Article  CAS  Google Scholar 

  17. G.W. Wang, C.S. Jia, Y.W. Dong, Tetrahedron Lett. 47, 1059 (2006)

    Article  CAS  Google Scholar 

  18. Nitin.T. Patil, F. Nawaz Khan, Y. Yamamoto, Tetrahedron Lett. 45, 8497 (2004)

    Article  CAS  Google Scholar 

  19. F. Nawaz Khan, R. Jayakumar, C.N. Pillai, J. Mol. Cat. A 195, 139 (2003)

    Article  CAS  Google Scholar 

  20. F. Nawaz Khan, R. Jayakumar, C.N. Pillai, Tetrahedron Lett. 43, 6807 (2002)

    Article  CAS  Google Scholar 

  21. P. Manivel, S. Mohana Roopan, F. Nawaz Khan, J. Chil. Chem. Soc. 53, 1609 (2008)

    Article  CAS  Google Scholar 

  22. Venkatesha R. Hathwar, P. Manivel, F. Nawaz Khan, T.N. Guru Row, Acta Cryst. E63, o3708 (2007)

    CAS  Google Scholar 

  23. S. Syed Tajudeen, F. Nawaz Khan, Synth. Commun. 37, 3649 (2007)

    Article  Google Scholar 

  24. P. Manivel, K. Prabakaran, F.N. Khan, J.S. Jin, Res. Chem. Intermed. doi:10.1007/s11164-011-0351-6

Download references

Acknowledgments

Authors are grateful to VIT University, Vellore, for providing research facilities. The authors wish to express their gratitude to SAIF, Indian Institute of Technology, Chennai, for their support of NMR and HRMS.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Fazlur-Rahman Nawaz Khan.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Krishnakumar, V., Khan, FR.N., Mandal, B.K. et al. Quinoline-3-carboxylates as potential antibacterial agents. Res Chem Intermed 38, 1819–1826 (2012). https://doi.org/10.1007/s11164-012-0505-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-0505-1

Keywords

Navigation