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Synthesis and Antibacterial Activity of Sulfanilamides Containing Sterically Hindered Phenol Fragments

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Abstract

New sulfanilamide derivatives containing sterically hindered phenol fragments have been synthesized via modification of the amino group by reaction with 3,5-di-tert-butyl-4-hydroxybenzyl acetate and diazotization followed by diazo coupling with 2,4-di-tert-butylphenol. 4-Aminobenzenesulfonamide derivatives at the sulfonamide group have been obtained by converting acetyl-protected 4-aminobenzenesulfonyl chloride to the corresponding sulfonohydrazide and reacting the latter with 3,5-di-tert-butyl-4-hydroxybenzyl acetate, sterically hindered hydroxybenzaldehydes, and N-(3,5-di-tert-butyl-4-hydroxybenzyl)isatin. Modification of sulfanilamide with sterically hindered phenol fragments significantly increased antibacterial activity.

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ACKNOWLEDGMENTS

The authors thank the Joint Spectral and Analytical Center for Physicochemical Study of the Structure and Properties of Substances and Materials (Kazan Scientific Center, Russian Academy of Sciences) for technical support.

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Authors and Affiliations

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

    S. V. Bukharov, A. R. Burilov, R. G. Tagasheva, G. N. Nugumanova, E. V. Nikitina & N. A. Mukmeneva

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

    A. R. Burilov

  3. Research Center of Pharmaceutics, Kazan (Volga region) Federal University, 420008, Kazan, Russia

    E. V. Nikitina

Authors
  1. S. V. Bukharov
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  2. A. R. Burilov
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  3. R. G. Tagasheva
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  4. G. N. Nugumanova
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  5. E. V. Nikitina
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  6. N. A. Mukmeneva
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Corresponding author

Correspondence to R. G. Tagasheva.

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The authors declare the absence of conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 10, pp. 1429–1437 https://doi.org/10.31857/S0514749221100086.

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Bukharov, S.V., Burilov, A.R., Tagasheva, R.G. et al. Synthesis and Antibacterial Activity of Sulfanilamides Containing Sterically Hindered Phenol Fragments. Russ J Org Chem 57, 1621–1627 (2021). https://doi.org/10.1134/S1070428021100080

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  • DOI: https://doi.org/10.1134/S1070428021100080

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