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Synthesis and Study of Antimicrobial Activity of Water-Soluble Ammonium Acylhydrazones Based on New 1,ω-Alkylenebis(isatins)

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Abstract

Alkylation of isatin with 1,ω-dihaloalkanes afforded bis(heterocycles) connected by an oligomethylene linker. The reaction of the resulting bis(isatins) with Girard’s T and Girard’s P reagents led to the formation of symmetrical water-soluble acyl hydrazones with high yields. Evaluation of antimicrobial activity of new compounds showed the dependence of the activity level on the hydrocarbon spacer length. The selective activity of nona- and decamethylene derivatives was established with respect to gram-positive bacteria S. aureus 209p and B. cereus 8035. Low hematotoxicity of the obtained heterocycles was revealed.

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Acknowledgements

The authors are grateful to the Center for Collective Use of the Spectral and Analytical Center of the Federal Research Center “Kazan Research Center of the Russian Academy of Sciences” for the technical support of the research.

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Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Science, ul. Akademika Arbuzova 8, Kazan, Tatarstan, 420088, Russia

    A. V. Bogdanov, I. F. Zaripova, L. K. Mustafina, A. D. Voloshina, A. S. Sapunova, N. V. Kulik & V. F. Mironov

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  1. A. V. Bogdanov
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  2. I. F. Zaripova
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  3. L. K. Mustafina
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  4. A. D. Voloshina
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  5. A. S. Sapunova
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  6. N. V. Kulik
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  7. V. F. Mironov
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Correspondence to A. V. Bogdanov.

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To the 70th Anniversary of A. V. Kuchin

Russian Text © The Author(s), 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 7, pp. 1004–1012.

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Bogdanov, A.V., Zaripova, I.F., Mustafina, L.K. et al. Synthesis and Study of Antimicrobial Activity of Water-Soluble Ammonium Acylhydrazones Based on New 1,ω-Alkylenebis(isatins). Russ J Gen Chem 89, 1368–1376 (2019). https://doi.org/10.1134/S107036321907003X

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