2-Aryl-1-hydroxyimidazoles possessing antiviral activity against wide range of orthopoxviruses including Variola virus

Basanova, E.I.; Kulikova, E.; Bormotov, N.I.; Serova, O.; Shishkina, L.; Ovchinnikova, A.; Odnoshevskiy, D.; Pyankov, O.; Agafonov, A.; Yarovaya, O.; Borisevich, S.; Ilyina, M.; Kolybalov, D.; Arkhipov, S.; Bogdanov, N.; Pavlova, M.A.; Salakhutdinov, N.; Perevalov, V.P.; Nikitina, P.A.

Авторы: Basanova Elizaveta Ivanovna, Kulikova Ekaterina, Bormotov Nikolai I., Serova Olga, Shishkina Larisa, Ovchinnikova Alyona, Odnoshevskiy Dmitry, Pyankov Oleg, Agafonov Alexander, Yarovaya Olga, Borisevich Sophia, Ilyina Margarita, Kolybalov Dmitry, Arkhipov Sergey, Bogdanov Nikita, Pavlova Marina A., Salakhutdinov Nariman, Perevalov Valery P., Nikitina Polina A.
Журнал: RSC Medicinal Chemistry
Год издания: 2024
Издательство: Royal Society of Chemistry
Местоположение издательства: United Kingdom
DOI: 10.1039/d4md00181h
Аннотация: Scientific interest in orthopoxvirus infections and search for new highly effective compounds possessing antiviral activity against orthopoxviruses has significantly increased as a result of multi-country world-wide mpox outbreak in 2022. Present work deals with the synthesis of new 2-arylimidazoles exhibiting in vitro activity not only against the Vaccinia virus, the Cowpox virus and the Ectromelia (mousepox) virus but also against the Variola virus. Out of imidazole derivatives under consideration (1-hydroxyimidazoles, 1-methoxyimidazoles, 1-benzyloxyimidazoles, imidazole N-oxides) the most perspective antiviral activity is demonstrated by 1-hydroxyimidazoles that may exist as two prototropic tautomers. Both of these tautomers may be manifested in different crystal structures of these compounds, according to single-crystal X-ray diffraction analysis, while predominantly one of them (N-hydroxy-tautomeric form) is present in DMSO-d6 solutions and gaseous state as shown by NMR spectroscopy and quantum-chemical calculations.The leader compound 1-hydroxy-2-(4-nitrophenyl)imidazole 4a demonstrated the highest selectivity indices both against the Vaccinia virus (SI = 1072) and the Variola virus (SI = 373).
Добавил в систему: Басанова Елизавета Ивановна

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№	Имя	Имя файла	Размер	Добавлен
1.	экспертное заключение	экспертное_Med_Chem.pdf	185,6 КБ	11 июля 2024 [ZakharkoMA]
2.	Первая страница	SSRN-id4619442-1.pdf	127,8 КБ	11 июля 2024 [ZakharkoMA]
3.	благодарности	SSRN-id4619442-37.pdf	110,9 КБ	11 июля 2024 [ZakharkoMA]

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2-Aryl-1-hydroxyimidazoles possessing antiviral activity against wide range of orthopoxviruses including Variola virusстатья

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