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Synthesis and Antimicrobial Activity Evaluation of Ammonium Acylhydrazones Based on 4,6-Di-tert-butyl-2,3-dihydroxybenzaldehyde

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Abstract

The condensation reaction of 4,6-di-tert-butyl-2,3-dihydroxybenzaldehyde with some ammonium acetohydrazides yielded water-soluble acylhydrazones with different structures of the cationic center. It was shown that in relation to Staphylococcus aureus, Bacillus cereus and Enterococcus faecalis, trimethylammonium chloride derivative exhibits activity at or above the level of comparison drugs, norfloxacin and chloramphenicol, respectively. The resulting compounds do not have a toxic effect on erythrocytes and normal human liver cells. The high activity of diethylmethylammonium acylhydrazone against the formation of biofilms formed by clinical staphylococci strains was shown for the first time. The high efficiency of new compounds in inhibiting the growth of phytopathogens of bacterial and fungal origin was established.

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ACKNOWLEDGMENTS

The authors are grateful to the Spectro-Analytical Center of the Kazan Scientific Center of the Russian Academy of Sciences for the technical support of the research.

Funding

The work was supported by the Strategic Academic Leadership Program of the Kazan (Volga Region) Federal University (Prioritet-2030). The study of antiphytopathogenic activity was carried out within the framework of the Program of Fundamental Scientific Research of the Russian Academy of Sciences (subject No. 121031100266-3, O.M. Tsivileva).

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Authors and Affiliations

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

    A. V. Bogdanov

  2. Kazan National Research Technological University, 420015, Kazan, Russia

    S. V. Bukharov & R. A. Garifullina

  3. A. E.Arbuzov Institute of Organic and Physical Chemistry, Federal Reseatch Center “Kazan Scientific Center of the Russian Academy of Sciences”, 420088, Kazan, Russia

    A. D. Voloshina, A. P. Lyubina & S. K. Amerkhanova

  4. Saratov State Vavilov Agrarian University, 410005, Saratov, Russia

    M. S. Bezsonova & Z. Yu. Khaptsev

  5. Institute of Biochemistry and Physiology of Plants and Microorganisms, Federal Research Center “Saratov Scientific Center of the Russian Academy of Sciences”, 410049, Saratov, Russia

    O. M. Tsivileva

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  1. A. V. Bogdanov
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  2. S. V. Bukharov
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  3. R. A. Garifullina
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  4. A. D. Voloshina
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  9. O. M. Tsivileva
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To Memory of V.I. Galkin

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Bogdanov, A.V., Bukharov, S.V., Garifullina, R.A. et al. Synthesis and Antimicrobial Activity Evaluation of Ammonium Acylhydrazones Based on 4,6-Di-tert-butyl-2,3-dihydroxybenzaldehyde. Russ J Gen Chem 92, 1875–1886 (2022). https://doi.org/10.1134/S1070363222100012

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