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Synthesis, structure investigation and evaluation of anti-orthopoxvirus activities of 2-(2-arylethenyl)imidazolesстатья
Информация о цитировании статьи получена из
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 23 января 2026 г.
- Авторы: Golfarb-Abramov Vladislav O., Kazennova Anastasia V., Basanova Elizaveta I., Serova Olga A., Bormotov Nikolai I., Shishkina Larisa N., Krasnov Vyacheslav I., Polovyanenko Dmitriy N., Moskalev Ivan A., Fedorov Alexey Yu, Arkhipov Sergey G., Ilyina Margarita G., Borisevich Sophia S., Yarovaya Olga I., Nikitina Polina A.
- Журнал: New Journal of Chemistry
- Том: 49
- Номер: 45
- Год издания: 2025
- Издательство: Royal Society of Chemistry
- Местоположение издательства: United Kingdom
- Первая страница: 19699
- Последняя страница: 19717
- DOI: 10.1039/d5nj03203b
- Аннотация: The continuing worldwide mpox outbreak (2022–present) provokes interest in the search for new small organic molecules possessing anti-viral activity against orthopoxviruses. In the course of this search a series of new 2-(2-arylethenyl)imidazoles were synthesized. Structural features of these derivatives were studied by means of NMR spectroscopy and single-crystal X-ray diffraction analysis. It was not surprising that all the title compounds were trans-isomers. Prevailing tautomers for 2-(2-arylethenyl)-1-hydroxyimidazoles were determined. If a carbonyl-containing substituent was present at position 5 of the imidazole, then the compound existed predominantly in a N-hydroxy-tautomeric form both in the gaseous phase and in solution in polar aprotic solvents. In crystal form, either a single N-hydroxy-tautomer or a mixture of both tautomers (N-hydroxyimidazole and imidazole N-oxide) were observed. For 2-(2-arylethenyl)-1-hydroxy-4,5-dimethylimidazoles in solution in polar aprotic solvents an equilibrium mixture of both tautomers in rapid interconversion was registered. Predominant conformers were determined for the 1-hydroxyimidazoles, 1-methoxyimidazoles, and 1-methylimidazole 3-oxides under consideration. Cytotoxicity and virus-inhibiting activity against Vaccinia virus were evaluated in vitro for all the imidazole derivatives under study. 2-(2-Arylethenyl)-1-methoxyimidazoles were determined to be the most promising. They also exhibited activities against zoonotic orthopoxviruses such as Cowpox virus and Mousepox (Ectromelia) virus. The lead compound 1-(1-methoxy-4-methyl-2-((E)-2-(4-nitrophenyl)ethenyl)-1H-imidazol-5-yl)ethanone 4b demonstrated the highest selectivity index against Vaccinia virus (SI = 305).
- Добавил в систему: Гольфарб-Абрамов Владислав Олегович