Skip to main content
Log in

Synthesis and antimicrobial activity of quaternary N-aryl-5,6-benzoquinaldinium derivatives

  • Published:
Pharmaceutical Chemistry Journal Aims and scope

A series of quaternary N-aryl-5,6-benzoquinaldinium derivatives have been synthesized. Their antimicrobial activity (E. coli, S. aureus) has been tested. It was found that introduction of a new annelated benzene ring into the heterocyclic molecule (compared with quinolinium and benzoquinolinium compounds) leads to a significant increase of the antibacterial activity. Electron-withdrawing substituents in the quaternary phenyl group decrease slightly the antimicrobial effect. Since better results have been obtained for N-phenyl-5,6-benzoquinaldinium tetrafluoroborate, biological investigations were continued on the additional test cultures S. saprophyticus, Salmonella spp., Micrococcus luteus, Proteus vulgaris, Bacillus subtilis, and Candida albicans. The observation of high fungicidal activity against C. albicans was promising.

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. E. S. Cherkasskii, L. R. Kolomeitsev, A. K. Sheikman, and I. T. Korneeva, Dokl. Akad. Nauk SSSR, 161(5), 1208 – 1211 (1965).

    PubMed  CAS  Google Scholar 

  2. T. N. Bennett, M. Paguio, B. Gligorijevic, et al., Antimicrob. Agents Chemother., 48(5), 1807 – 1810 (2004).

    Article  PubMed  CAS  Google Scholar 

  3. T. Zhao and G. Sun, J. Surfactants Deterg., 9, 325 – 330 (2006).

    Article  CAS  Google Scholar 

  4. K. M. Docherty and C. F. Kulpa, Jr., Green Chem., No. 7, 185 – 189 (2005).

  5. B. M. Gutsulyak, Usp. Khim., 41(2), 346 – 373 (1972).

    CAS  Google Scholar 

  6. I. I. Sidorchuk, R. F. Stadniichuk, E. N. Tishchenko, and L. T. Bordyakovskaya, Khim.-farm. Zh., 12(7), 78 – 80 (1978).

    CAS  Google Scholar 

  7. W. S. Chen, G. H. Cocolas, C. J. Cavallito, and K. J. Chai, J. Med. Chem., 20(12), 1617 – 1623 (1977).

    Article  PubMed  CAS  Google Scholar 

  8. W. S. Chen, G. H. Cocolas, and C. J. Cavallito, J. Pharm. Sci., 68(8), 1025 – 1027 (1979).

    Article  PubMed  CAS  Google Scholar 

  9. J. W. Bunting, K. R. Laderoute, and D. J. Norris, Can. J. Biochem., 49 – 57 (1980).

  10. P. V. Prisyazhnyuk, G. K. Palii, Yu. L. Volyanskii, et al., Khim.-farm. Zh., 10(5), 46 – 49 (1976).

    Google Scholar 

  11. T. Zhao and G. Sun, J. Appl. Microbiol., 1 – 7 (2007).

  12. G. T. Pilyugin and E. P. Opanasenko, Ukr. Khim. Zh., 18(6), 625 – 630 (1952).

    CAS  Google Scholar 

  13. G. T. Pilyugin and E. P. Opanasenko, Zh. Obshch. Khim., 27, 1015 – 1018 (1957).

    CAS  Google Scholar 

  14. E. Knoevenagel, J. Prakt. Chem., 89(1), 1 – 50 (1913).

    Article  Google Scholar 

  15. G. N. Pershin (ed.), Methods of Experimental Chemotherapy [in Russian], Medgiz, Moscow (1971), p. 109.

Download references

Acknowledgments

The work was supported financially by the RFBR, Grant No. 10-03-00685-a.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to N. E. Shchepina.

Additional information

Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 45, No. 3, pp. 30 – 32, March, 2011.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shchepina, N.E., Boiko, I.I. & Aleksandrova, G.A. Synthesis and antimicrobial activity of quaternary N-aryl-5,6-benzoquinaldinium derivatives. Pharm Chem J 45, 159–161 (2011). https://doi.org/10.1007/s11094-011-0583-1

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11094-011-0583-1

Key words

Navigation