| Autor: |
Basanova, Elizaveta I., Kulikova, Ekaterina A., Bormotov, Nikolai I., Serova, Olga A., Shishkina, Larisa N., Ovchinnikova, Alyona S., Odnoshevskiy, Dmitry A., Pyankov, Oleg V., Agafonov, Alexander P., Yarovaya, Olga I., Borisevich, Sophia S., Ilyina, Margarita G., Kolybalov, Dmitry S., Arkhipov, Sergey G., Bogdanov, Nikita E., Pavlova, Marina A., Salakhutdinov, Nariman F., Perevalov, Valery P., Nikitina, Polina A. |
| Zdroj: |
MedChemComm; 2024, Vol. 15 Issue: 9 p3196-3211, 16p |
| Abstrakt: |
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 vitroactivity 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-d6solutions and in the gaseous state, as shown by NMR spectroscopy and quantum-chemical calculations. The leader compound 1-hydroxy-2-(4-nitrophenyl)imidazole 4ademonstrated the highest selectivity indices against the vaccinia virus (SI = 1072) and the variola virus (SI = 373). |
| Databáze: |
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