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2-Aryl-1-hydroxyimidazoles Possessing Antiviral Activity Against a Wide Range of Orthopoxviruses, Including Variola Virus. Научная публикация

Журнал RSC Medicinal Chemistry
ISSN: 2632-8682
Вых. Данные Год: 2024, Том: 15, Номер: 9, Страницы: 3196-3211 Страниц : 16 DOI: 10.1039/d4md00181h
Авторы Basanova Elizaveta I. 1 , Kulikova Ekaterina A. 1 , Bormotov Nikolai I. 2 , Serova Olga A. 2 , Shishkina Larisa N. 2 , Ovchinnikova Alyona S. 2 , Odnoshevskiy Dmitry A. 2 , Pyankov Oleg V. 2 , Agafonov Alexander P. 2 , Yarovaya Olga I. 3 , Borisevich Sophia S. 4 , Ilyina Margarita G. 4 , Kolybalov Dmitry S. 5 , Arkhipov Sergey G. 5 , Bogdanov Nikita E. 5,6 , Pavlova Marina A. 7 , Salakhutdinov Nariman F. 3 , Perevalov Valery P. 1 , Nikitina Polina A. 1
Организации
1 Department of Fine Organic Synthesis and Chemistry of Dyes, D.I. Mendeleev University of Chemical Technology of Russia, Miusskaya sq., 9, 125047, Moscow, Russia
2 State Research Center of Virology and Biotechnology VECTOR, Rospotrebnadzor, 630559, Koltsovo, Russia
3 Department of Medicinal Chemistry, N.N. Vorozhtsov Institute of Organic Chemistry SB RAS, Lavrentyev Ave., 9, 630090, Novosibirsk, Russia
4 SRF “SKIF”, 630559, Koltsovo, Russia
5 Scientific Educational Center “Institute of Chemical Technology”, Novosibirsk State University, Pirogova str., 1, 630090, Novosibirsk, Russia
6 V.S. Sobolev Institute of Geology and Mineralogy, Siberian Branch of Russian Academy of Sciences, Koptyuga Ave., 3, 630090 Novosibirsk, Russia
7 Laboratory of Photoactive Supramolecular Systems, A.N. Nesmeyanov Institute of Organoelement Compounds RAS, Vavilova str., 28, 119991, Moscow, Russia

Информация о финансировании (2)

1 Министерство науки и высшего образования Российской Федерации (с 15 мая 2018) 075-15-2021-1355 (121120100401-9)
2 Министерство науки и высшего образования Российской Федерации (с 15 мая 2018) FWUR-2024-0040

Реферат: Scientific interest in orthopoxvirus infections and search for new highly effective compounds possessing antiviral activity against orthopoxviruses have significantly increased as a result of worldwide mpox outbreak in 2022. The present work deals with the synthesis of new 2-arylimidazoles exhibiting in vitro activity not only against the vaccinia virus, cowpox virus and ectromelia (mousepox) virus but also against the variola virus. Among the imidazole derivatives under consideration (1-hydroxyimidazoles, 1-methoxyimidazoles, 1-benzyloxyimidazoles, and imidazole N-oxides), the most promising antiviral activity is demonstrated by 1-hydroxyimidazoles, which 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 in the 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 against the vaccinia virus (SI = 1072) and the variola virus (SI = 373).
Библиографическая ссылка: Basanova E.I. , Kulikova E.A. , Bormotov N.I. , Serova O.A. , Shishkina L.N. , Ovchinnikova A.S. , Odnoshevskiy D.A. , Pyankov O.V. , Agafonov A.P. , Yarovaya O.I. , Borisevich S.S. , Ilyina M.G. , Kolybalov D.S. , Arkhipov S.G. , Bogdanov N.E. , Pavlova M.A. , Salakhutdinov N.F. , Perevalov V.P. , Nikitina P.A.
2-Aryl-1-hydroxyimidazoles Possessing Antiviral Activity Against a Wide Range of Orthopoxviruses, Including Variola Virus.
RSC Medicinal Chemistry. 2024. V.15. N9. P.3196-3211. DOI: 10.1039/d4md00181h WOS Scopus OpenAlex СКИФ ID
Даты:
Поступила в редакцию: 15 мар. 2024 г.
Принята к публикации: 25 июн. 2024 г.
Опубликована online: 5 июл. 2024 г.
Опубликована в печати: 1 сент. 2024 г.
Идентификаторы БД:
Web of science: WOS:001290822300001
Scopus: 2-s2.0-85201419997
OpenAlex: W4400366884
СКИФ ID: 3526
Цитирование в БД: Пока нет цитирований
Альметрики: