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Biologically Active Symmetric and Asymmetric Dicationic Bis(isatin hydrazones): What is Better―To Complicate or Simplify the Spacer?

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Abstract

The reaction of bisisatins containing a 1,ω-alkylene, -arylene, or -alkyluracil spacer with ammonium acetohydrazides gave a series of symmetric and asymmetric dicationic isatin-3-acylhydrazones. It was shown that the antimicrobial activity of the new compounds depends on the structure of the spacer and the nature of the substituent in the aromatic fragment. 5-Substituted isatin derivatives, where the heterocyclic fragments are linked by an 9- and 10-carbon alkylene chains, exhibit bactericidal effect against resistant strains of S. aureus at the level of Norfloxacin and the fungal pathogen P. cactorum, which causes plant late blight.

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ACKNOWLEDGMENTS

The authors express their gratitude to the Center for Collective Use and Control, Kazan Research Center, Russian Academy of Sciences, for technical support of the research. The study was carried out within the framework of the state assignment for of the Kazan Research Center, Russian Academy of Sciences. The antiphytopathogenic activity testing (O.M. Tsivileva) was carried out within the framework of the state assignment for the Saratov Research Center, Russian Academy of Sciences, from the Ministry of Education and Science of the Russian Federation (topic no. 121031100266-3).

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This work was supported by ongoing institutional funding. No additional grants to carry out or direct this particular research were obtained.

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Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center, Russian Academy of Sciences, 420088, Kazan, Russia

    A. V. Bogdanov, A. D. Voloshina, S. K. Amerkhanova & V. F. Mironov

  2. Institute of Biochemistry and Physiology of Plants and Microorganisms, Saratov Research Center, Russian Academy of Sciences (IBPPM RAS), 410049, Saratov, Russia

    O. M. Tsivileva

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

    R. R. Rakhmatullin

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  1. A. V. Bogdanov
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Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 11, pp. 1387–1409 https://doi.org/10.31857/S0514749223110010.

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Bogdanov, A.V., Voloshina, A.D., Amerkhanova, S.K. et al. Biologically Active Symmetric and Asymmetric Dicationic Bis(isatin hydrazones): What is Better―To Complicate or Simplify the Spacer?. Russ J Org Chem 59, 1831–1850 (2023). https://doi.org/10.1134/S1070428023110015

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