Skip to main content
Log in

Synthesis and Antimicrobial Activity of New Dialkyl(diaryl)-2-(5-chloro-2-hydroxyphenyl)-2-(phenylethenyl)pentylphosphonium Salts

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

An Erratum to this article was published on 01 March 2019

This article has been updated

Abstract

New dialkyl(diaryl)-2-(5-chloro-2-hydroxyphenyl)-2-(phenylethenyl)pentylphosphonium salts bearing various substituents at the phosphorus atom were synthesized. Antimicrobial activity of the salts obtained was estimated. Derivatives with 2-methoxyphenyl substituents at the phosphorus atom are most active against grampositive bacteria. Herewith, dibenzyl-substituted phosphonium derivatives possess the best antifungal 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

Change history

  • 25 April 2019

    The row in the table on p. 1802 for compound <Emphasis Type="Bold">8a</Emphasis> should be as follows:

References

  1. Carmona-Ribeiro, A. and de Melo Carrasco, L., Int. J. Mol. Sci., 2013, vol. 14, no. 5, p. 9906. doi 10.3390/ijms14059906

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Deka, S., Sharma, A., and Kumar, P., Curr. Top. Med. Chem., 2015, vol. 15, no. 13, p. 1179. doi 10.2174/1568026615666150330110602

    Article  CAS  PubMed  Google Scholar 

  3. Kaur, R. and Liu, S., Prog. Surf. Sci., 2016, vol. 91, no. 3, p. 136. doi 10.1016/j.progsurf.2016.09.001

    Article  CAS  Google Scholar 

  4. Nazarov, P.A., Osterman, I.A., Tokarchuk, A.V., Karakozova, M.V., Korshunova, G.A., Lyamzaev, K.G., Skulachev, M.V., Kotova, E.A., Skulachev, V.P., and Antonenko, Y.N., Sci. Rep., 2017, vol. 7, no. 1, p. 1394. doi 10.1038/s41598-017-00802-8

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Khasiyatullina, N.R., Vazykhova, A.M., Mironov, V.F., Krivolapov, D.B., Voronina, Y.K., Voloshina, A.D., Kulik, N.V., and Strobykina, A.S., Mendeleev Commun., 2017, vol. 27, no. 2, p. 134. doi 10.1016/j.mencom.2017.03.008

    Article  CAS  Google Scholar 

  6. Strobykina, I.Y., Belenok, M.G., Semenova, M.N., Semenov, V.V., Babaev, V.M., Rizvanov, I.K., Mironov, V.F., and Kataev, V.E., J. Nat. Prod., 2015, vol. 78, no. 6, p. 1300. doi 10.1021/acs.jnatprod.5b00124

    Article  CAS  PubMed  Google Scholar 

  7. Testai, L., Strobykina, I., Semenov, V.V., Semenova, M., Da Pozzo, E., Martelli, A., Citi, V., Martini, C., Breschi, M.C., Kataev, V.E., and Calderone, V., Int. J. Mol. Sci., 2017, vol. 18, no. 10, p. 2060. doi 10.3390/ijms18102060

    Article  CAS  PubMed Central  Google Scholar 

  8. Tsepaeva, O.V., Nemtarev, A.V., Abdullin, T.I., Grigor’eva, L.R., Kuznetsova, E.V., Akhmadishina, R.A., Ziganshina, L.E., Cong, H.H., and Mironov, V.F., J. Nat. Prod., 2017, vol. 80, no. 8, p. 2232. doi 10.1021/acs.jnatprod.7b00105

    Article  CAS  PubMed  Google Scholar 

  9. Zielonka, J., Joseph, J., Sikora, A., Hardy, M., Ouari, O., Vasquez-Vivar, J., Cheng, G., Lopez, M., and Kalyanaraman, B., Chem. Rev., 2017, vol. 117, no. 15, p. 10043. doi10.1021/acs.chemrev.7b00042

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Franklin, T.J. and Snow, G.A., Biochemistry of Antimicrobial Action, Dordrecht: Springer, 1989, p. 216. doi 10.1007/978-94-009-0825-3

    Book  Google Scholar 

  11. Hill, E.H., Whitten, D.G., and Evans, D.G., J. Phys. Chem. (B), 2014, vol. 118, no. 32, p. 9722. doi 10.1007/978-94-009-0825-3

    Article  CAS  Google Scholar 

  12. Kanazawa, A., Ikeda, T., and Endo, T., Antimicrob. Agents Chemother., 1994, vol. 38, no. 5, p. 945. doi 10.1128/AAC.38.5.945

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Lukáč, M., Devínsky, F., Pisárčik, M., Papapetropoulou, A., Bukovský, M., and Horváth, B., J. Surfactants Deterg., 2017, vol. 20, no. 1, p. 159. doi 10.1007/s11743-016-1908-6

    Article  CAS  Google Scholar 

  14. Kanazawa, A. and Ikeda, T., Coord. Chem. Rev., 2000, vol. 198, no. 1, p. 117. doi 10.1016/S0010-8545(99) 00224-6

    Article  CAS  Google Scholar 

  15. Zhu, D., Cheng, H., Li, J., Zhang, W., Shen, Y., Chen, S., Ge, Z., and Chen, S., Mater. Sci. Eng. (C), 2016, vol. 61, p. 79. doi 10.1016/j.msec.2015.12.024

    Article  CAS  Google Scholar 

  16. Tatarinov, D.A., Kuznetsov, D.M., Voloshina, A.D., Lyubina, A.P., Strobykina, A.S., Mukhitova, F.K., Polyancev, F.M., and Mironov, V.F., Tetrahedron, 2016, vol. 72, no. 51, p. 8493. doi 10.1016/j.tet.2016.11.023

    Article  CAS  Google Scholar 

  17. Ramirez, F., Bigler, A.J., and Smith, C.P., Tetrahedron, 1968, vol. 24, no. 14, p. 5041. doi 10.1016/S0040-4020 (01)88414-3

    Article  CAS  Google Scholar 

  18. Mironov, V.F., Konovalov, A.I., Litvinov, I.A., Gubaidullin, A.T., Petrov, R.R., Shtyrlina, A.A., Zyablikova, T.A., Musin, R.Z., Azancheev, N.M., and Il’yasov, A.V., Russ. J. Gen. Chem., 1998, vol. 68, no. 9, p. 1414.

    CAS  Google Scholar 

  19. Mironov, V.F., Tatarinov, D.A., Varaksina, E.N., Baronova, T.A., Zagidullina, I.Ya., Mustafina, A.R., Konovalov, A.I., C. A., 2008, vol. 149, 153215.

  20. Tatarinov, D.A., Mironov, V.F., Varaksina, E.N., and Konovalov, A.I., Russ. J. Gen. Chem., 2008, vol. 78, no. 6, p. 1287. doi 10.1134/S1070363208060340

    Article  CAS  Google Scholar 

  21. Tatarinov, D.A., Kuznetsov, D.M., and Mironov, V.F., Russ. J. Org. Chem., 2014, vol. 50, no. 4, p. 544. doi 10.1134/S1070428014040174

    Article  CAS  Google Scholar 

  22. National Committee for Clinical Laboratory Standards, Methods for Dilution Antimicrobial Susceptibility. Tests for Bacteria that Grow Aerobically, Wayne, 2000.

  23. National Committee for Clinical Laboratory Standards, Reference Method for Broth Dilution Antifungal Susceptibility Testing of Conidium-Forming Filamentous Fungi, Wayne, 1998.

  24. Semenov, V.E., Mikhailov, A.S., Voloshina, A.D., Kulik, N.V, Nikitashina, A.D., Zobov, V.V, Kharlamov, S.V, Latypov, S.K., and Reznik, V.S., Eur. J. Med. Chem., 2011, vol. 46, no. 9, p. 4715. doi 10.1016/j.ejmech.2011.05.034

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to D. A. Tatarinov.

Additional information

Dedicated to the 110th anniversary of M.I. Kabachnik’s birth

Original Russian Text © D.A. Tatarinov, N.V. Terekhova, A.D. Voloshina, A.S. Sapunova, A.P. Lyubina, V.F. Mironov, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 9, pp. 1453–1459.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tatarinov, D.A., Terekhova, N.V., Voloshina, A.D. et al. Synthesis and Antimicrobial Activity of New Dialkyl(diaryl)-2-(5-chloro-2-hydroxyphenyl)-2-(phenylethenyl)pentylphosphonium Salts. Russ J Gen Chem 88, 1800–1805 (2018). https://doi.org/10.1134/S1070363218090062

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363218090062

Keywords

Navigation