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

IF 0.8 4区化学 Q4 CHEMISTRY, MULTIDISCIPLINARY

Russian Journal of General Chemistry Pub Date : 2025-10-07 DOI:10.1134/S1070363225604739

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

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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.

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超亲电活化条件下氟化2-苄基苯并咪唑的合成及其抗菌性能研究

氟化2-羟基甲基苯并咪唑与苯在br / nsted超强酸CF3SO3H中在140℃下反应2.5 h，得到相应的2-羟基甲基苯并咪唑，产率为61 ~ 73%。根据实验核磁共振研究和理论DFT计算，该反应中的关键反应性亲电试剂是起始苯并咪唑的n -质子化o -原溶剂化形式。对起始和靶氟苯并咪唑对大肠杆菌和金黄色葡萄球菌以及酵母样真菌白色念珠菌的抑菌活性进行了评估。这些化合物对白色念珠菌具有最高的生物活性。

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来源期刊

Russian Journal of General Chemistry 化学-化学综合

CiteScore

1.40

自引率

22.20%

发文量

252

审稿时长

2-4 weeks

期刊介绍： Russian Journal of General Chemistry is a journal that covers many problems that are of general interest to the whole community of chemists. The journal is the successor to Russia’s first chemical journal, Zhurnal Russkogo Khimicheskogo Obshchestva (Journal of the Russian Chemical Society ) founded in 1869 to cover all aspects of chemistry. Now the journal is focused on the interdisciplinary areas of chemistry (organometallics, organometalloids, organoinorganic complexes, mechanochemistry, nanochemistry, etc.), new achievements and long-term results in the field. The journal publishes reviews, current scientific papers, letters to the editor, and discussion papers.