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Abstract <p>Fluorinated 2-hydroxymethylbenzimidazoles reacted with benzene in the Brønsted superacid CF<sub>3</sub>SO<sub>3</sub>H at 140C in 2.5 h to afford the corresponding 2-benzylbenzimidazoles in yields of 61–73%. According to experimental NMR studies and theoretical DFT calculations, the key reactive electrophiles in this reaction are <i>N</i>-protonated <i>O</i>-protosolvated forms of starting benzimidazoles. Antimicrobial activity against <i>Escherichia coli</i> and <i>Staphylococcus aureus</i> bacteria, as well as yeast-like fungi <i>Candida albicans</i> was evaluated for the starting and target fluorinated benzimidazoles. These compounds exhibited the highest biological activity in relation to <i>Candida albicans</i> fungi.</p>

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Synthesis of Fluorinated 2-Benzylbenzimidazoles Under Superelectrophilic Activation Conditions and Investigation of Their Antimicrobial Properties

  • 期刊论文

  • 发表日期：

    2025年9月1日

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  • Veronika I. Fadeeva,
  • Dmitry S. Ryabukhin,
  • Mikhail V. Kalyaev,
  • Larisa V. Politanskaya,
  • Vasily E. Romanov,
  • Nadezhda M. Troshkova,
  • Irina A. Boyarskaya,
  • Alexander Yu. Ivanov,
  • Kristina E. Borovkova,
  • Sofiya A. Brevnova,
  • Karina S. Gromozdova,
  • Dgirgal P. Turbeeva,
  • Aleksander V. Vasilyev

摘要

Abstract

Fluorinated 2-hydroxymethylbenzimidazoles reacted with benzene in the Brønsted superacid CF3SO3H at 140C in 2.5 h to afford the corresponding 2-benzylbenzimidazoles in yields of 61–73%. According to experimental NMR studies and theoretical DFT calculations, the key reactive electrophiles in this reaction are N-protonated O-protosolvated forms of starting benzimidazoles. Antimicrobial activity against Escherichia coli and Staphylococcus aureus bacteria, as well as yeast-like fungi Candida albicans was evaluated for the starting and target fluorinated benzimidazoles. These compounds exhibited the highest biological activity in relation to Candida albicans fungi.