Sciact
  • EN
  • RU

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

Journal RSC Medicinal Chemistry
ISSN: 2632-8682
Output data Year: 2024, Volume: 15, Number: 9, Pages: 3196-3211 Pages count : 16 DOI: 10.1039/d4md00181h
Authors 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
Affiliations
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

Funding (2)

1 Ministry of Science and Higher Education of the Russian Federation 075-15-2021-1355 (121120100401-9)
2 Ministry of Science and Higher Education of the Russian Federation FWUR-2024-0040

Abstract: 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).
Cite: 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 publication_identifier_short.sciact_skif_identifier_type
Dates:
Submitted: Mar 15, 2024
Accepted: Jun 25, 2024
Published online: Jul 5, 2024
Published print: Sep 1, 2024
Identifiers:
Web of science: WOS:001290822300001
Scopus: 2-s2.0-85201419997
OpenAlex: W4400366884
publication_identifier.sciact_skif_identifier_type: 3526
Citing: Пока нет цитирований
Altmetrics: