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2-Aryl-1-hydroxyimidazoles possessing antiviral activity against a wide range of orthopoxviruses, including the variola virus. / Басанова, Елизавета И.; Куликова, Екатерина А.; Бормотов, Николай И. et al.

In: RSC Medicinal Chemistry, Vol. 15, No. 9, 05.07.2024, p. 3196-3211.

Research output: Contribution to journal › Article › peer-review

Harvard

Басанова, ЕИ, Куликова, ЕА, Бормотов, НИ, Серова, ОА, Шишкина, ЛН, Овчинникова, АС, Одношевский, ДА, Пьянков, ОВ, Агафонов, АП, Яровая, ОИ, Борисевич, СС, Ильина, МГ, Колыбалов, ДС, Архипов, СГ, Богданов, НЕ, Павлова, МА, Салахутдинов, НФ, Перевалов, ВП & Никитина, ПА 2024, '2-Aryl-1-hydroxyimidazoles possessing antiviral activity against a wide range of orthopoxviruses, including the variola virus', RSC Medicinal Chemistry, vol. 15, no. 9, pp. 3196-3211.

APA

Басанова, Е. И., Куликова, Е. А., Бормотов, Н. И., Серова, О. А., Шишкина, Л. Н., Овчинникова, А. С., Одношевский, Д. А., Пьянков, О. В., Агафонов, А. П., Яровая, О. И., Борисевич, С. С., Ильина, М. Г., Колыбалов, Д. С., Архипов, С. Г., Богданов, Н. Е., Павлова, М. А., Салахутдинов, Н. Ф., Перевалов, В. П., & Никитина, П. А. (2024). 2-Aryl-1-hydroxyimidazoles possessing antiviral activity against a wide range of orthopoxviruses, including the variola virus. RSC Medicinal Chemistry, 15(9), 3196-3211.

Vancouver

Басанова ЕИ, Куликова ЕА, Бормотов НИ, Серова ОА, Шишкина ЛН, Овчинникова АС et al. 2-Aryl-1-hydroxyimidazoles possessing antiviral activity against a wide range of orthopoxviruses, including the variola virus. RSC Medicinal Chemistry. 2024 Jul 5;15(9):3196-3211.

Author

Басанова, Елизавета И. ; Куликова, Екатерина А. ; Бормотов, Николай И. et al. / 2-Aryl-1-hydroxyimidazoles possessing antiviral activity against a wide range of orthopoxviruses, including the variola virus. In: RSC Medicinal Chemistry. 2024 ; Vol. 15, No. 9. pp. 3196-3211.

BibTeX

@article{22f82359d312471c9b2c1f3726773ab5,
title = "2-Aryl-1-hydroxyimidazoles possessing antiviral activity against a wide range of orthopoxviruses, including the variola virus",
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).",
author = "Басанова, {Елизавета И.} and Куликова, {Екатерина А.} and Бормотов, {Николай И.} and Серова, {Ольга А.} and Шишкина, {Лариса Н.} and Овчинникова, {Алёна С.} and Одношевский, {Дмитрий А.} and Пьянков, {Олег В.} and Агафонов, {Александр П.} and Яровая, {Ольга И.} and Борисевич, {Софья С.} and Ильина, {Маргарита Г.} and Колыбалов, {Дмитрий С.} and Архипов, {Сергей Г.} and Богданов, {Никита Е.} and Павлова, {Марина А.} and Салахутдинов, {Нариман Ф.} and Перевалов, {Валерий П.} and Никитина, {Полина А.}",
note = "We thank the multi-access chemical research center SB RAS for spectral and analytical measurements. The contribution of the Center for Molecular Composition Studies of the Institute of Organoelement Compounds RAS is also gratefully acknowledged. Crystallographic research was supported by the Ministry of Science and Higher Education of the Russian Federation (Agreement No. 075-15-2021-1355 dated 12 October 2021) as part of the implementation of certain activities of the Federal Scientific and Technical Program for the Development of Synchrotron and Neutron Research and Research Infrastructure for 2019\u20132027. Also, this work was partially supported by the Ministry of Science and Higher Education of the Russian Federation within the governmental order for SRF SKIF Boreskov Institute of Catalysis (project FWUR-2024-0040). Biological testing in the orthopoxviruses has been carried out with the State assignment of the State Research Centre of Virology and Biotechnology VECTOR.",
year = "2024",
month = jul,
day = "5",
language = "English",
volume = "15",
pages = "3196--3211",
journal = "RSC Medicinal Chemistry",
issn = "2632-8682",
publisher = "Royal Society of Chemistry",
number = "9",

}

RIS

TY - JOUR

T1 - 2-Aryl-1-hydroxyimidazoles possessing antiviral activity against a wide range of orthopoxviruses, including the variola virus

AU - Басанова, Елизавета И.

AU - Куликова, Екатерина А.

AU - Бормотов, Николай И.

AU - Серова, Ольга А.

AU - Шишкина, Лариса Н.

AU - Овчинникова, Алёна С.

AU - Одношевский, Дмитрий А.

AU - Пьянков, Олег В.

AU - Агафонов, Александр П.

AU - Яровая, Ольга И.

AU - Борисевич, Софья С.

AU - Ильина, Маргарита Г.

AU - Колыбалов, Дмитрий С.

AU - Архипов, Сергей Г.

AU - Богданов, Никита Е.

AU - Павлова, Марина А.

AU - Салахутдинов, Нариман Ф.

AU - Перевалов, Валерий П.

AU - Никитина, Полина А.

N1 - We thank the multi-access chemical research center SB RAS for spectral and analytical measurements. The contribution of the Center for Molecular Composition Studies of the Institute of Organoelement Compounds RAS is also gratefully acknowledged. Crystallographic research was supported by the Ministry of Science and Higher Education of the Russian Federation (Agreement No. 075-15-2021-1355 dated 12 October 2021) as part of the implementation of certain activities of the Federal Scientific and Technical Program for the Development of Synchrotron and Neutron Research and Research Infrastructure for 2019\u20132027. Also, this work was partially supported by the Ministry of Science and Higher Education of the Russian Federation within the governmental order for SRF SKIF Boreskov Institute of Catalysis (project FWUR-2024-0040). Biological testing in the orthopoxviruses has been carried out with the State assignment of the State Research Centre of Virology and Biotechnology VECTOR.

PY - 2024/7/5

Y1 - 2024/7/5

N2 - 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).

AB - 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).

UR - http://scopus.com/record/display.uri?eid=2-s2.0-85201419997&origin=inward&txGid=0b004f4d872301374cfe188ee3142263

M3 - Article

VL - 15

SP - 3196

EP - 3211

JO - RSC Medicinal Chemistry

JF - RSC Medicinal Chemistry

SN - 2632-8682

IS - 9

ER -

ID: 60862171