Standard

FeCl3⋅6H2O-mediated cyclization of fluorinated 2’-hydroxychalcones in alcohol medium into flavanones with antiviral activity. / Wang, Jiaying; Politanskaya, Larisa; Selivanov, Boris et al.

In: Journal of Fluorine Chemistry, Vol. 280, 110371, 11.2024.

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

Harvard

Wang, J, Politanskaya, L, Selivanov, B, Esaulkova, I, Volobueva, A & Zarubaev, V 2024, 'FeCl3⋅6H2O-mediated cyclization of fluorinated 2’-hydroxychalcones in alcohol medium into flavanones with antiviral activity', Journal of Fluorine Chemistry, vol. 280, 110371. https://doi.org/10.1016/j.jfluchem.2024.110371

APA

Wang, J., Politanskaya, L., Selivanov, B., Esaulkova, I., Volobueva, A., & Zarubaev, V. (2024). FeCl3⋅6H2O-mediated cyclization of fluorinated 2’-hydroxychalcones in alcohol medium into flavanones with antiviral activity. Journal of Fluorine Chemistry, 280, [110371]. https://doi.org/10.1016/j.jfluchem.2024.110371

Vancouver

Wang J, Politanskaya L, Selivanov B, Esaulkova I, Volobueva A, Zarubaev V. FeCl3⋅6H2O-mediated cyclization of fluorinated 2’-hydroxychalcones in alcohol medium into flavanones with antiviral activity. Journal of Fluorine Chemistry. 2024 Nov;280:110371. doi: 10.1016/j.jfluchem.2024.110371

Author

Wang, Jiaying ; Politanskaya, Larisa ; Selivanov, Boris et al. / FeCl3⋅6H2O-mediated cyclization of fluorinated 2’-hydroxychalcones in alcohol medium into flavanones with antiviral activity. In: Journal of Fluorine Chemistry. 2024 ; Vol. 280.

BibTeX

@article{387d379223a548c9b481568ca4a1858d,
title = "FeCl3⋅6H2O-mediated cyclization of fluorinated 2{\textquoteright}-hydroxychalcones in alcohol medium into flavanones with antiviral activity",
abstract = "A simple, inexpensive and efficient approach for the synthesis of fluorinated 2-arylchroman-4-ones from corresponding 2′-hydroxychalcones has been realized. The reactions are successfully conducted in presence of FeCl3⋅6H2O in EtOH at 100 °C. It was found that the same transformation takes place in the reaction system FeCl3⋅6H2O/MeOH/100 °C. In contrast, the use of FeCl3⋅6H2O in MeOH at 150 °C leads to the oxidative cyclization of 2′-hydroxychalcones to form 2-arylchromen-4-ones. A some of the obtained fluorinated flavanones were evaluated for their inhibitory activity against influenza A virus A/Puerto Rico/8/34 (H1N1) in the MDCK cell culture. Among the studied heterocycles 6,7-difluoro-2-(4-methoxyphenyl)chroman-4-one exhibited the highest anti-influenza virus activity (IC50 = 11.4 μM, SI = 91). ",
keywords = "Anti-influenza virus activity, FeCl3⋅6H2O, Fluorinated flavanones, Heterocyclisation of 2′-hydroxychalcones, Oxidation and chlorination of flavanones",
author = "Jiaying Wang and Larisa Politanskaya and Boris Selivanov and Iana Esaulkova and Alexandrina Volobueva and Vladimir Zarubaev",
note = "This work was supported by the Ministry of Science and Higher Education of the Russian Federation (project 122040400035-3) FeCl3⋅6H2O-mediated cyclization of fluorinated 2{\textquoteright}-hydroxychalcones in alcohol medium into flavanones with antiviral activity / J. Wang, L. Politanskaya, B. Selivanov [et al.] // Journal of Fluorine Chemistry. – 2024. – Vol. 280. – P. 110371. – DOI 10.1016/j.jfluchem.2024.110371. ",
year = "2024",
month = nov,
doi = "10.1016/j.jfluchem.2024.110371",
language = "English",
volume = "280",
journal = "Journal of Fluorine Chemistry",
issn = "0022-1139",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - FeCl3⋅6H2O-mediated cyclization of fluorinated 2’-hydroxychalcones in alcohol medium into flavanones with antiviral activity

AU - Wang, Jiaying

AU - Politanskaya, Larisa

AU - Selivanov, Boris

AU - Esaulkova, Iana

AU - Volobueva, Alexandrina

AU - Zarubaev, Vladimir

N1 - This work was supported by the Ministry of Science and Higher Education of the Russian Federation (project 122040400035-3) FeCl3⋅6H2O-mediated cyclization of fluorinated 2’-hydroxychalcones in alcohol medium into flavanones with antiviral activity / J. Wang, L. Politanskaya, B. Selivanov [et al.] // Journal of Fluorine Chemistry. – 2024. – Vol. 280. – P. 110371. – DOI 10.1016/j.jfluchem.2024.110371.

PY - 2024/11

Y1 - 2024/11

N2 - A simple, inexpensive and efficient approach for the synthesis of fluorinated 2-arylchroman-4-ones from corresponding 2′-hydroxychalcones has been realized. The reactions are successfully conducted in presence of FeCl3⋅6H2O in EtOH at 100 °C. It was found that the same transformation takes place in the reaction system FeCl3⋅6H2O/MeOH/100 °C. In contrast, the use of FeCl3⋅6H2O in MeOH at 150 °C leads to the oxidative cyclization of 2′-hydroxychalcones to form 2-arylchromen-4-ones. A some of the obtained fluorinated flavanones were evaluated for their inhibitory activity against influenza A virus A/Puerto Rico/8/34 (H1N1) in the MDCK cell culture. Among the studied heterocycles 6,7-difluoro-2-(4-methoxyphenyl)chroman-4-one exhibited the highest anti-influenza virus activity (IC50 = 11.4 μM, SI = 91).

AB - A simple, inexpensive and efficient approach for the synthesis of fluorinated 2-arylchroman-4-ones from corresponding 2′-hydroxychalcones has been realized. The reactions are successfully conducted in presence of FeCl3⋅6H2O in EtOH at 100 °C. It was found that the same transformation takes place in the reaction system FeCl3⋅6H2O/MeOH/100 °C. In contrast, the use of FeCl3⋅6H2O in MeOH at 150 °C leads to the oxidative cyclization of 2′-hydroxychalcones to form 2-arylchromen-4-ones. A some of the obtained fluorinated flavanones were evaluated for their inhibitory activity against influenza A virus A/Puerto Rico/8/34 (H1N1) in the MDCK cell culture. Among the studied heterocycles 6,7-difluoro-2-(4-methoxyphenyl)chroman-4-one exhibited the highest anti-influenza virus activity (IC50 = 11.4 μM, SI = 91).

KW - Anti-influenza virus activity

KW - FeCl3⋅6H2O

KW - Fluorinated flavanones

KW - Heterocyclisation of 2′-hydroxychalcones

KW - Oxidation and chlorination of flavanones

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85210022294&origin=inward&txGid=510a699cd197e2edc4009cd18b97fb62

UR - https://www.mendeley.com/catalogue/39d93404-f30d-3dc8-b07d-6100e2368e73/

UR - https://elibrary.ru/item.asp?id=79241793

U2 - 10.1016/j.jfluchem.2024.110371

DO - 10.1016/j.jfluchem.2024.110371

M3 - Article

VL - 280

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

SN - 0022-1139

M1 - 110371

ER -

ID: 61105047