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Fluorinated 2-arylchroman-4-ones and their derivatives: synthesis, structure and antiviral activity. / Troshkova, Nadezhda; Politanskaya, Larisa; Bagryanskaya, Irina и др.

в: Molecular Diversity, 2023.

Результаты исследований: Научные публикации в периодических изданияхстатьяРецензирование

Harvard

Troshkova, N, Politanskaya, L, Bagryanskaya, I, Chuikov, I, Wang, J, Ilyina, P, Mikhalski, M, Esaulkova, I, Volobueva, A & Zarubaev, V 2023, 'Fluorinated 2-arylchroman-4-ones and their derivatives: synthesis, structure and antiviral activity', Molecular Diversity. https://doi.org/10.1007/s11030-023-10769-6

APA

Troshkova, N., Politanskaya, L., Bagryanskaya, I., Chuikov, I., Wang, J., Ilyina, P., Mikhalski, M., Esaulkova, I., Volobueva, A., & Zarubaev, V. (2023). Fluorinated 2-arylchroman-4-ones and their derivatives: synthesis, structure and antiviral activity. Molecular Diversity. https://doi.org/10.1007/s11030-023-10769-6

Vancouver

Troshkova N, Politanskaya L, Bagryanskaya I, Chuikov I, Wang J, Ilyina P и др. Fluorinated 2-arylchroman-4-ones and their derivatives: synthesis, structure and antiviral activity. Molecular Diversity. 2023. Epub 2023 дек. 28. doi: 10.1007/s11030-023-10769-6

Author

Troshkova, Nadezhda ; Politanskaya, Larisa ; Bagryanskaya, Irina и др. / Fluorinated 2-arylchroman-4-ones and their derivatives: synthesis, structure and antiviral activity. в: Molecular Diversity. 2023.

BibTeX

@article{e680cc457e8c4e5d95308792cf1c1597,
title = "Fluorinated 2-arylchroman-4-ones and their derivatives: synthesis, structure and antiviral activity",
abstract = "A number of new biologically interesting fluorinated 2-arylchroman-4-ones and their 3-arylidene derivatives were synthesized based on the p-toluenesulfonic acid-catalyzed one-pot reaction of 2-hydroxyacetophenones with benzaldehydes. It was found that obtained (E)-3-arylidene-2-aryl-chroman-4-ones reacted with malononitrile under base conditions to form 4,5-diaryl-4H,5H-pyrano[3,2-c]chromenes. The structures of the synthesized fluorinated compounds were confirmed by 1H, 19F, and 13C NMR spectral data, and for some representatives of heterocycles also using NOESY spectra and X-ray diffraction analysis. A large series of obtained flavanone derivatives as well as products of their modification (35 examples) containing from 1 to 12 fluorine atoms in the structure was tested in vitro for cytotoxicity in MDCK cell line and for antiviral activity against influenza A virus. Among the studied heterocycles 6,8-difluoro-2-(4-(trifluoromethyl)phenyl)chroman-4-one (IC50 = 6 μM, SI = 150) exhibited the greatest activity against influenza A/Puerto Rico/8/34 (H1N1) virus. Moreover, this compound appeared active against phylogenetically distinct influenza viruses, A(H5N2) and influenza B (SI's of 53 and 42, correspondingly). The data obtained suggest that the fluorinated derivatives of 2-arylchroman-4-ones are prospective scaffolds for further development of potent anti-influenza antivirals.",
keywords = "4,5-Diaryl-4H,5H-pyrano[3,2-c]chromenes, Anti-viral activity, Cycloaddition, Fluorinated flavanones, Influenza virus, p-Toluenesulfonic acid",
author = "Nadezhda Troshkova and Larisa Politanskaya and Irina Bagryanskaya and Igor Chuikov and Jiaying Wang and Polina Ilyina and Mikhail Mikhalski and Iana Esaulkova and Alexandrina Volobueva and Vladimir Zarubaev",
note = "The authors thank the Multi-Access Chemical Service Center SB RAS for spectral and analytical measurements, and the Russian Science Foundation (Project No. 23-23-00008) for financial support. {\textcopyright} 2023. The Author(s), under exclusive licence to Springer Nature Switzerland AG.",
year = "2023",
doi = "10.1007/s11030-023-10769-6",
language = "English",
journal = "Molecular Diversity",
issn = "1381-1991",
publisher = "Springer Netherlands",

}

RIS

TY - JOUR

T1 - Fluorinated 2-arylchroman-4-ones and their derivatives: synthesis, structure and antiviral activity

AU - Troshkova, Nadezhda

AU - Politanskaya, Larisa

AU - Bagryanskaya, Irina

AU - Chuikov, Igor

AU - Wang, Jiaying

AU - Ilyina, Polina

AU - Mikhalski, Mikhail

AU - Esaulkova, Iana

AU - Volobueva, Alexandrina

AU - Zarubaev, Vladimir

N1 - The authors thank the Multi-Access Chemical Service Center SB RAS for spectral and analytical measurements, and the Russian Science Foundation (Project No. 23-23-00008) for financial support. © 2023. The Author(s), under exclusive licence to Springer Nature Switzerland AG.

PY - 2023

Y1 - 2023

N2 - A number of new biologically interesting fluorinated 2-arylchroman-4-ones and their 3-arylidene derivatives were synthesized based on the p-toluenesulfonic acid-catalyzed one-pot reaction of 2-hydroxyacetophenones with benzaldehydes. It was found that obtained (E)-3-arylidene-2-aryl-chroman-4-ones reacted with malononitrile under base conditions to form 4,5-diaryl-4H,5H-pyrano[3,2-c]chromenes. The structures of the synthesized fluorinated compounds were confirmed by 1H, 19F, and 13C NMR spectral data, and for some representatives of heterocycles also using NOESY spectra and X-ray diffraction analysis. A large series of obtained flavanone derivatives as well as products of their modification (35 examples) containing from 1 to 12 fluorine atoms in the structure was tested in vitro for cytotoxicity in MDCK cell line and for antiviral activity against influenza A virus. Among the studied heterocycles 6,8-difluoro-2-(4-(trifluoromethyl)phenyl)chroman-4-one (IC50 = 6 μM, SI = 150) exhibited the greatest activity against influenza A/Puerto Rico/8/34 (H1N1) virus. Moreover, this compound appeared active against phylogenetically distinct influenza viruses, A(H5N2) and influenza B (SI's of 53 and 42, correspondingly). The data obtained suggest that the fluorinated derivatives of 2-arylchroman-4-ones are prospective scaffolds for further development of potent anti-influenza antivirals.

AB - A number of new biologically interesting fluorinated 2-arylchroman-4-ones and their 3-arylidene derivatives were synthesized based on the p-toluenesulfonic acid-catalyzed one-pot reaction of 2-hydroxyacetophenones with benzaldehydes. It was found that obtained (E)-3-arylidene-2-aryl-chroman-4-ones reacted with malononitrile under base conditions to form 4,5-diaryl-4H,5H-pyrano[3,2-c]chromenes. The structures of the synthesized fluorinated compounds were confirmed by 1H, 19F, and 13C NMR spectral data, and for some representatives of heterocycles also using NOESY spectra and X-ray diffraction analysis. A large series of obtained flavanone derivatives as well as products of their modification (35 examples) containing from 1 to 12 fluorine atoms in the structure was tested in vitro for cytotoxicity in MDCK cell line and for antiviral activity against influenza A virus. Among the studied heterocycles 6,8-difluoro-2-(4-(trifluoromethyl)phenyl)chroman-4-one (IC50 = 6 μM, SI = 150) exhibited the greatest activity against influenza A/Puerto Rico/8/34 (H1N1) virus. Moreover, this compound appeared active against phylogenetically distinct influenza viruses, A(H5N2) and influenza B (SI's of 53 and 42, correspondingly). The data obtained suggest that the fluorinated derivatives of 2-arylchroman-4-ones are prospective scaffolds for further development of potent anti-influenza antivirals.

KW - 4,5-Diaryl-4H,5H-pyrano[3,2-c]chromenes

KW - Anti-viral activity

KW - Cycloaddition

KW - Fluorinated flavanones

KW - Influenza virus

KW - p-Toluenesulfonic acid

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85180658523&origin=inward&txGid=97ebff90ccec344f599d88c4ed3ec1e5

UR - https://www.mendeley.com/catalogue/4e0f8e1c-0ad6-36e6-b541-73f24c06ebdf/

U2 - 10.1007/s11030-023-10769-6

DO - 10.1007/s11030-023-10769-6

M3 - Article

C2 - 38153637

JO - Molecular Diversity

JF - Molecular Diversity

SN - 1381-1991

ER -

ID: 59533515