Skip to main content
SpringerLink
Log in

Construction of 1,3-disubstituted 4-oxo-1,4-dihydroquinolines as a potential antibacterial agents

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

Abstract

A novel series of 1,3-disubstituted 4-oxo-1,4-dihydroquinolines as antimicrobial agents were designed and synthesized. Their structures have been confirmed using spectroscopic analyses (IR, NMR, and EI-MS). Most of the newly prepared compounds were screened for their antimicrobial activities against two Gram-positive bacterial strains and six Gram-negative bacterial strains. Many of the synthesized compounds displayed a high antimicrobial activity in comparison with reference drugs, for example compounds 4–6, 15, 17, and 18.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Scheme 2
Scheme 3
Scheme 4
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. G.S. Tillotson, J. Med. Microbiol. 44, 320 (1996)

    Article  CAS  Google Scholar 

  2. S. Sabatini, F. Gosetto, G. Manfroni, O. Tabarrini, G.W. Kaatz, D. Patel, V. Cecchetti, Med. Chem. 54, 5722 (2011)

    Article  CAS  Google Scholar 

  3. S. Srinivasan, R.M.B. Shafreen, P. Nithyanand, P. Manisankar, S.K. Pandian, Eur. J. Med. Chem. 45, 6101 (2010)

    Article  CAS  Google Scholar 

  4. Y. Wang, G.L.V. Damu, J.S. Lv, R.X. Geng, D.C. Yang, C.H. Zhou, Bioorg. Med. Chem. Lett. 22, 5363 (2012)

    Article  CAS  Google Scholar 

  5. A. Aecadi, M. Chiarini, S. D. Giuseppe, F. Marinelli, Synletter 203 (2003)

  6. J. Wiesner, R. Ortmann, H. Jomaa, M. Schlitzer, Angew. Chem. Int. Ed. 42, 5274 (2003)

    Article  CAS  Google Scholar 

  7. M. Kidwai, K.R. Bhushan, P. Sapra, R.K. Saxena, R. Gupta, Bioorg. Med. Chem. 8, 69 (2000)

    Article  CAS  Google Scholar 

  8. L.S. Redgrave, S.B. Sutton, M.A. Webber, L.J.V. Piddock, Trends Microbiol. 22, 438 (2014)

    Article  CAS  Google Scholar 

  9. D.C. Hooper, Clin. Infect. Dis. 32, S9 (2001)

    Article  CAS  Google Scholar 

  10. G.J. Pruss, R.J. Franco, S.G. Chevalier, S.H. Manes, K. Drlic, Bacteriol. 168, 276 (1986)

    Article  CAS  Google Scholar 

  11. K. Drlica, Trends Genet. 6, 433 (1990)

    Article  CAS  Google Scholar 

  12. K. Drlica, Curr. Opin. Microbiol. 2, 504 (1999)

    Article  CAS  Google Scholar 

  13. K. Drlica, H. Hiasa, R. Kerns, M. Malik, A. Mustaev, X. Zhao, Curr. Top. Med. Chem. 9, 981 (2009)

    Article  CAS  Google Scholar 

  14. K. Drlica, M. Malik, R.J. Kerns, X. Zhao, Antimicrob. Agents Chemother. 52, 385 (2008)

    Article  CAS  Google Scholar 

  15. K. Yasuhiro, N. Shuichiro, M. Shinobu, H. Shunso, M. Haruyo, Y, Akira, PCT Int. Appl. WO 9313091 (1993)

  16. F.A. El-Essawy, W.A. El-Sayed, Heterocyclic Chem. 50, E1 (2013)

    Article  CAS  Google Scholar 

  17. B.S. Jayashree, S. Thomas, Y. Nayak, Med. Chem. Res. 19, 193 (2010)

    Article  CAS  Google Scholar 

  18. J. Boström, A. Hogner, A. Llinàs, E. Wellner, A.T. Plowright, Med. Chem. 55, 1817 (2012)

    Article  Google Scholar 

  19. Y. Li, J. Geng, Y. Lui, S. Yu, G. Zhao, Med. Chem. 81, 27 (2013)

    Google Scholar 

  20. Clinical and Laboratory Standards Institute. Performance standards for antimicrobial susceptibility testing; Twenty-Fourth informational supplement, (M100-S24).Wayne, USA, pp: 34(1), 1 (2014)

  21. A. Rodloff, T. Bauer, S. Ewig, P. Kujath, E. Müller, Deutsches Ärzteblatt Int 105, 657 (2008)

    Google Scholar 

Download references

Acknowledgments

The authors would like to thank Professor Gerhard Maas from Institute of Organic Chemistry I, University of Ulm, Germany for assistance with NMR measurements. We are indebted to Prince Sattam Bin Abdulaziz University, King of Saudi Arabia for helping with fin Chemicals.

Author information

Author notes

  1. Nader M. Boshta

    Present address: Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, An der Immenburg 4, 53121, Bonn, Germany

Authors and Affiliations

  1. Preparatory Year Deanship, Basic Science Department, Prince Sattam Bin Abdulaziz University, 151, Al-Kharj, 11942, Saudi Arabia

    Farag A. El-Essawy

  2. Chemistry Department, Faculty of Science, Menoufia University, Shebin El-Koam, Egypt

    Farag A. El-Essawy, Nader M. Boshta & Ebtsam A. Saleh

  3. Department of Chemistry, Collage of Science and Humanities, Prince Sattam Bin Abdulaziz University, 83, Al-Kharj, 11942, Saudi Arabia

    Mshari A. Alotaibi

  4. Department of Bacteriology, Mycology and Immunology, Faculty of Veterinary Medicine, University of Sadat City, Menoufia, Egypt

    Mohamed S. Elsayed & Reda Tarabees

Authors
  1. Farag A. El-Essawy
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Nader M. Boshta
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mshari A. Alotaibi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Mohamed S. Elsayed
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Reda Tarabees
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Ebtsam A. Saleh
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Nader M. Boshta.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

El-Essawy, F.A., Boshta, N.M., Alotaibi, M.A. et al. Construction of 1,3-disubstituted 4-oxo-1,4-dihydroquinolines as a potential antibacterial agents. Res Chem Intermed 42, 8157–8174 (2016). https://doi.org/10.1007/s11164-016-2586-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-016-2586-8

Keywords

Search

Navigation