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Synthesis and Biological Activity of Phosphorylated Quaternary Ammonium Salts

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Abstract

A series of phosphorylated quaternary ammonium salts (QASs) containing isobutyl substituents on the phosphorus atom and higher alkyl substituents on the nitrogen atom were prepared in two steps. The QASs containing octyl to tetradecyl substituents on the nitrogen atom showed high antimicrobial activity against B. cereus, S. aureus, and E. coli bacterial strains, as well as C. albicans fungal strain, whereas hexa- and octadecyl-substituted QASs were inactive against the test pathogenic strains of microorganisms. As shown by 31Р NMR spectroscopy, the synthesized QASs underwent hydrolysis in air to form the corresponding phosphorylated betaines.

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Funding

This paper has been supported by the Kazan Federal University Strategic Academic Leadership Program (“PRIORITY-2030”).

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Authors and Affiliations

  1. Kazan (Volga Region) Federal University, 420008, Kazan, Russia

    A. M. Gayneev, R. R. Davletshin, I. V. Galkina, N. V. Davletshina, N. O. Kuznetsov & A. N. Sedov

  2. Kazan State Medical Academy, 420012, Kazan, Russia

    M. P. Shulaeva

Authors
  1. A. M. Gayneev
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  2. R. R. Davletshin
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  3. I. V. Galkina
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  4. N. V. Davletshina
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  5. N. O. Kuznetsov
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  6. A. N. Sedov
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  7. M. P. Shulaeva
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Correspondence to A. M. Gayneev.

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Additional information

Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 5, pp. 672–678 https://doi.org/10.31857/S0514749223050154.

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Gayneev, A.M., Davletshin, R.R., Galkina, I.V. et al. Synthesis and Biological Activity of Phosphorylated Quaternary Ammonium Salts. Russ J Org Chem 59, 840–845 (2023). https://doi.org/10.1134/S1070428023050159

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  • DOI: https://doi.org/10.1134/S1070428023050159

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