Skip to main content
SpringerLink
Log in

Synthesis and study of antimicrobial activity of quaternary ammonium benzofuroxan salts

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

It was found that quaternary ammonium salts of benzofuroxan based on o-, m-, and p-dibromoxylenes are formed as a mixture of two tautomers. Only one bromomethyl group participates in the quaternization of benzofuroxan with different dibromoxylenes. Bacteriostatic activity of the most active mixture of tautomers was two and four times higher than the reference drug, chloramphenicol, with respect to Staphylococcus aureus 209p and Bacillus cereus 8035, correspondingly. Hemolysis of these compounds does not exceed 1%, i.e., such compounds are not toxic.

Graphical abstract

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
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Fischbach MA (2011) Curr Opin Chem Microbiol 14:519

    Article  CAS  Google Scholar 

  2. Allahverdiyev AM, Kon KV, Abamor ES, Bagirova M, Rafailovich M (2011) Expert Rev Anti Infect Ther 9:1035

    Article  CAS  Google Scholar 

  3. Domagk G (1938) Preserving and disinfecting compositions. US Patent 2,108,765, Feb 15, 1938; (1938) Chem Abstr 32:22129

  4. Campoccia D, Montanaro L, Arciola CR (2006) Biomaterials 27:2331

    Article  CAS  Google Scholar 

  5. McDonnell G, Russell AD (1999) Clin Microbiol Rev 12:147

    CAS  Google Scholar 

  6. Dong H, Huang J, Koepse RR, Ye P, Russell AJ, Matyjaszewski K (2011) Biomacromol 12:1305

    Article  CAS  Google Scholar 

  7. Jovene C, Chugunova EA, Goumont R (2013) Mini Rev Med Chem 13:1089

    Article  CAS  Google Scholar 

  8. Chugunova E, Burilov A (2017) Curr Top Med Chem 17:986

    Article  CAS  Google Scholar 

  9. Jones ML, Ganopolsky JG, Labbe A, Wahl C, Prakash S (2010) Appl Microbiol Biotechnol 88:401

    Article  CAS  Google Scholar 

  10. Ghaffari A, Miller CC, McMullin B, Ghahary A (2006) Nitric Oxide 14:21

    Article  CAS  Google Scholar 

  11. Riccio DA, Schoenfisch MH (2012) Chem Soc Rev 41:3731

    Article  CAS  Google Scholar 

  12. Carpenter AW, Schoenfisch MH (2012) Chem Soc Rev 41:3742

    Article  CAS  Google Scholar 

  13. Hetrick EM, Shin JH, Stasko NA, Johnson CB, Wespe DA, Holmuhamedov E, Schoenfisch MH (2008) ACS Nano 2:235

    Article  CAS  Google Scholar 

  14. Carpenter AW, Slomberg DL, Rao KS, Schoenfisch MH (2011) ACS Nano 5:7235

    Article  CAS  Google Scholar 

  15. Chugunova E, Boga C, Sazykin I, Cino S, Micheletti G, Mazzanti A, Sazykina M, Burilov A, Khmelevtsova L, Kostina N (2015) Eur J Med Chem 93:349

    Article  CAS  Google Scholar 

  16. Chugunova E, Akylbekov N, Bulatova A, Gavrilov N, Voloshina A, Kulik N, Zobov V, Dobrynin A, Syakaev V, Burilov A (2016) Eur J Med Chem 116:165

    Article  CAS  Google Scholar 

  17. Chugunova E, Akylbekov N, Shakirova L, Dobrynin A, Syakaev V, Latypov S, Bukharov S, Burilov A (2016) Tetrahedron 72:6415

    Article  CAS  Google Scholar 

  18. Pashirova TN, Lukashenko SS, Zakharov SV, Voloshina AD, Zhiltsova EP, Zobov VV, Souto EB, Zakharova LY (2015) Colloids Surf B 127:266

    Article  CAS  Google Scholar 

  19. Yusupova LM, Molodykh ZV, Buzykin BI, Falyakhov IF, Anisimova NN, Sharnin GP, Bulidorov VV, Sviridov SI, Levinson FS (1995) 4- or 6-nitro-5,7-dichlorobenzofuroxan having fungicidal activity. RU Patent. 2,032,678, Apr 10, 1995; Chem Abstr 124:109724

  20. Sheldrick GM (1997) SADABS. Bruker AXS Inc, Madison

    Google Scholar 

  21. Altomare A, Cascarano G, Giacovazzo C, Viterbo D (1991) Acta Crystallogr A 47:744

    Article  Google Scholar 

  22. Sheldrick G (1997) SHELX-97: Programs for crystal structure analysis. Göttingen, Germany

    Google Scholar 

  23. Farrugia LJ (1999) J Appl Crystallogr 32:837

    Article  CAS  Google Scholar 

  24. APEX2 (Version 2.1) (2006) SAINTPlus. Data Reduction and Correction Program (Version 7.31A, Bruker Advanced X-ray Solutions, BrukerAXS Inc, Madison, Wisconsin, USA

  25. National Committee for Clinical Laboratory Standards (1998) Reference method for broth dilution antifungal susceptibility testing of conidium-forming filamentous fungi: proposed standard. NCCLS, Wayne, M38-P, Pa, USA

  26. National Committee for Clinical Laboratory Standards (2000) Methods for dilution antimicrobial susceptibility. Tests for bacteria that grow aerobically, sixth edition: approved standard. M7-A5, NCCLS, Wayne, Pa, USA

  27. Neese F (2012) Wiley Interdiscip Rev Comput Mol Sci 2:73

    Article  CAS  Google Scholar 

  28. Adamo C, Barone V (1999) J Chem Phys 110:6158

    Article  CAS  Google Scholar 

  29. Weigend F, Ahlrichs R (2005) Phys Chem Chem Phys 7:3297

    Article  CAS  Google Scholar 

  30. Grimme S, Antony J, Ehrlich S, Krieg H (2010) J Chem Phys 132:154104

    Article  Google Scholar 

  31. Becke AD, Johnson ER (2005) J Chem Phys 123:154101

    Article  Google Scholar 

  32. Johnson ER, Becke AD (2006) J Chem Phys 124:174104

    Article  Google Scholar 

  33. Grimme S, Ehrlich S, Goerigk L (2011) J Comput Chem 32:1456

    Article  CAS  Google Scholar 

  34. Barone V, Cossi M (1998) J Phys Chem A 102:1995

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the Russian Science Foundation (Grant No. 14-50-00014).

Author information

Authors and Affiliations

  1. A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Kazan, Russia

    Elena A. Chugunova, Alexandra D. Voloshina, Natalia V. Kulik, Vladimir V. Zobov, Anna G. Strelnik, Tatiana P. Gerasimova, Alexey B. Dobrynin & Alexander R. Burilov

  2. Kazan National Research Technological University, Kazan, Russia

    Nurgali I. Akylbekov & Essam M. Mahrous

Authors
  1. Elena A. Chugunova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Nurgali I. Akylbekov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Essam M. Mahrous
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Alexandra D. Voloshina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Natalia V. Kulik
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Vladimir V. Zobov
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Anna G. Strelnik
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Tatiana P. Gerasimova
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Alexey B. Dobrynin
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Alexander R. Burilov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Elena A. Chugunova.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 536 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Chugunova, E.A., Akylbekov, N.I., Mahrous, E.M. et al. Synthesis and study of antimicrobial activity of quaternary ammonium benzofuroxan salts. Monatsh Chem 149, 119–126 (2018). https://doi.org/10.1007/s00706-017-2052-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-017-2052-3

Keywords

Search

Navigation