Standard

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. https://doi.org/10.1039/d4md00181h

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. https://doi.org/10.1039/d4md00181h

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. doi: 10.1039/d4md00181h

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 Ивановна} and Борисевич, {Софья С.} and Ильина, {Маргарита Г.} and Колыбалов, {Дмитрий Сергеевич} and Архипов, {Сергей Григорьевич} and Богданов, {Никита Евгеньевич} and Павлова, {Марина А.} and Салахутдинов, {Нариман Фаридович} 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",
doi = "10.1039/d4md00181h",
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 Ивановна

AU - Борисевич, Софья С.

AU - Ильина, Маргарита Г.

AU - Колыбалов, Дмитрий Сергеевич

AU - Архипов, Сергей Григорьевич

AU - Богданов, Никита Евгеньевич

AU - Павлова, Марина А.

AU - Салахутдинов, Нариман Фаридович

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

U2 - 10.1039/d4md00181h

DO - 10.1039/d4md00181h

M3 - Article

C2 - 39165907

VL - 15

SP - 3196

EP - 3211

JO - RSC Medicinal Chemistry

JF - RSC Medicinal Chemistry

SN - 2632-8682

IS - 9

ER -

ID: 60862171