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- W4384405583 abstract "Favipiravir is an important selective antiviral against RNA-based viruses, and currently, it is being repurposed as a potential drug for the treatment of COVID-19. This type of chemical system presents different carboxamide-rotameric and hydroxyl-tautomeric states, which could be essential for interpreting its selective antiviral activity. Herein, the tautomeric 3-hydroxypyrazine/3-pyrazinone pair of favipiravir and its 6-substituted analogues, 6-Cl, 6-Br, 6-I, and 6-H, were fully investigated in solution and in the solid state through ultraviolet-visible, 1H nuclear magnetic resonance, infrared spectroscopy, and X-ray diffraction techniques. Also, a study of the gas phase was performed using density functional theory calculations. In general, the keto-enol balance in these 3-hydroxy-2-pyrazinecarboxamides is finely modulated by external and internal electrical variations via changes in solvent polarity or by replacement of substituents at position 6. The enol tautomer was prevalent in an apolar environment, whereas an increase in the level of the keto tautomer was favored by an increase in solvent polarity and, even moreso, with a strong hydrogen-donor solvent. Keto tautomerization was favored either in solution or in the solid state with a decrease in 6-substituent electronegativity as follows: H ≫ I ≈ Br > Cl ≥ F. Specific rotameric states based on carboxamide, cisoide and transoide, were identified for the enol and keto tautomer, respectively; their rotamerism is dependent on the tautomerism and not the aggregation state." @default.
- W4384405583 created "2023-07-16" @default.
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- W4384405583 date "2023-07-15" @default.
- W4384405583 modified "2023-09-30" @default.
- W4384405583 title "Tautomerism and Rotamerism of Favipiravir and Halogenated Analogues in Solution and in the Solid State" @default.
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- W4384405583 doi "https://doi.org/10.1021/acs.joc.3c00777" @default.
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- W4384405583 hasPublicationYear "2023" @default.
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