Skip to main content
Log in

Chiral Salts of Dithiophosphonic Acids on the Basis of Monoterpenyl Alcohols and Cinchona Alkaloids

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Reactions of O-terpenyl dithiophosphonic acids with cinchona alkaloids lead to the formation of quinuclidinium salts of these acids. Quinuclidinium salts possess antimicrobial activity against Bacillus cereus, Staphylococcus aureus and Candida albicans.

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.

Scheme
Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Zielinska-Blajet, M. and Skarzewski, J., Phosphorus, Sulfur, Silicon, Relat. Elem., 2013, vol. 188, p. 1811. https://doi.org/10.1080/10426507.2013.788000

    Article  CAS  Google Scholar 

  2. Gorecki, L., Berlicki, L., Mucha, A., Kafarski, P., Slepokura, K., and Rudzinska-Szostak, E., Chirality, 2012, vol. 24, p. 318. https://doi.org/10.1002/chir.22000

    Article  CAS  Google Scholar 

  3. Vannoorenberghe, Y. and Buono, G., Tetrahedron Lett., 1988, vol. 29, no. 26, p. 3235. https://doi.org/10.1016/0040-4039(88)85130-X

    Article  CAS  Google Scholar 

  4. Chodkiewicz, W., Jore, D., and Wodzki, W., Tetrahedron Lett., 1979, vol. 20, no. 12, p. 1069. https://doi.org/10.1016/S0040-4039(01)87194-X

    Article  Google Scholar 

  5. Mizuta, S., Sadamori, M., Fujimoto, T., and Yamamoto, I., Angew. Chem. Int. Ed., 2003, vol. 42, no. 29, p. 3383. https://doi.org/10.1002/anie.200250719

    Article  CAS  Google Scholar 

  6. Chodkiewicz, W., J. Organomet. Chem., 1984, vol. 273, no. 3, p. 55. https://doi.org/10.1016/0022-328X(84)80557-4

    Article  Google Scholar 

  7. Mizuta, S., Tsuzuki, T., Fujimoto, T., and Yamamoto, I., Org. Lett., 2005, vol. 7, no. 17. 3633. https://doi.org/10.1021/ol051129m

  8. Rudzińska-Szostak, E., Górecki, Ł., Berlicki, Ł., Ślepokura, K., and Mucha, A., Chirality, 2015, vol. 27, no. 10, p. 752. https://doi.org/10.1002/chir.22494

    Article  CAS  Google Scholar 

  9. Nizamov, I.S., Nikitin, E.N., Batyeva, E.S., Faskhetdinov, R.F., and Cherkasov, R.A., Russ. J. Org. Chem., 2015, vol. 51, no. 6, p. 899. https://doi.org/10.1134/S1070428015060147

    Article  CAS  Google Scholar 

  10. Nizamov, I.S., Salikhov, R.Z., Nizamov, I.D., Yakimov, V.Yu., Sergeenko, G.G., Batyeva, E.S., and Cherkasov, R.A., Russ. J. Gen. Chem., 2018, vol. 88, no. 11, p. 2307. https://doi.org/10.1134/S0044460X18110100

    Article  CAS  Google Scholar 

  11. Nizamov, I.S., Shumatbaev, G.G., Nizamov, I.D., Salikhov, R.Z., Nikitin, Ye.N., Shulaeva, M.P., Pozdeev, O.K., Batyeva, E.S., and Cherkasov, R.A., ChemistrySelect., 2019, vol. 4, p. 1681. https://doi.org/10.1002/slct.201802783

    Article  CAS  Google Scholar 

  12. Sofronov, A.V., Al’metkina, L.A., Nikitin, E.N., Nizamov, I.S., and Cherkasov, R.A., Russ. J. Org. Chem., 2010, vol. 46, no. 2, p. 300. https://doi.org/10.1134/S1070428009020260

    Article  CAS  Google Scholar 

  13. Al’metkina, L.A., Nizamov, I.S., Sofronov, A.V., Gabdullina, G.T., Cherkasov, R.A., Gurevich, P.A., Strunin, B.P., Satarova, L.F., and Antipov, V.A., Khim. Rast. Syr’ya, 2011, no. 4, p. 57.

    Google Scholar 

  14. Nizamov, I.S., Gabdullina, G.T., Al’metkina, L.A., Shamilov, R.R., Batyeva, E.S., and Cherkasov, R.A., Russ. J. Gen. Chem., 2012, vol. 82, no. 10, p. 1751. https://doi.org/10.1134/S1070363212100209

    Article  CAS  Google Scholar 

  15. Nizamov, I.S., Gabdullina, G.T., Al’metkina, L.A., Shamilov, R.R., and Cherkasov, R.A., Russ J. Gen. Chem., 2013, vol. 49, p. 145. https://doi.org/10.1134/S1070428013010247

    Article  CAS  Google Scholar 

  16. Cherkasov, R.A., Nizamov, I.S., Gabdullina, G.T., Almetkina, L.A., Shamilov, R.R., Sofronov, A.V., Phosphorus, Sulfur, Silicon, Relat. Elem., 2013, vol. 188, p. 33. https://doi.org/10.1080/10426507.2012.740697

    Article  CAS  Google Scholar 

  17. Crutchfield, M.M., Dungan, C.H., Letcher, J.H., Mark, V., Van Wazer, J.R. Topics in Phosphorus Chemistry. P31 Nuclear Magnetic Resonance, Grayson, M. and Griffith, E.J., New York: Wiley and Sons, 1967, vol. 5.

  18. Shagidullin, R.R., Chernova, A.V., Vinogradova, V.S., and Mukhametov, F.S., Atlas IK-spektrov fosfororganicheskikh soedinenii (interpretirovannye spektrogrammy) (Atlas of IR Spectra of Organophosphorus Compounds (Interpreted Spectrograms)), Moscow: Nauka, 1984.

Download references

ACKNOWLEDGMENTS

The authors are grateful to O.K. Pozdeev and M.P. Shulaeva (Kazan State Medical Academy) for carrying out antimicrobial studies. The authors are grateful to the staff of Distributed Spectral-Analytical Center of Shared Facilities for Study of Structure, Composition and Properties of Substances and Materials of Federal Research Center of Kazan Scientific Center of Russian Academy of Sciences» for the spectral studies and elemental analysis.

Funding

The work was carried out at the expense of a subsidy allocated to the Kazan (Volga region) Federal University for the completing the state task in the field of scientific activity (no. 0671-2020-0063), as well as within the framework of the state task of the Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences.”

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to I. S. Nizamov.

Ethics declarations

R.A. Cherkasov is a member of the editorial board of the Journal of General Chemistry. The other authors declare no conflicts of interest.

Additional information

To the 145th anniversary of A.E. Arbuzov

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nizamov, I.S., Yakovlev, A.A., Shilnikova, O.V. et al. Chiral Salts of Dithiophosphonic Acids on the Basis of Monoterpenyl Alcohols and Cinchona Alkaloids. Russ J Gen Chem 92, 2620–2630 (2022). https://doi.org/10.1134/S1070363222120106

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363222120106

Keywords:

Navigation