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FeCl3⋅6H2O-mediated cyclization of fluorinated 2’-hydroxychalcones in alcohol medium into flavanones with antiviral activity. / Wang, Jiaying; Politanskaya, Larisa; Selivanov, Boris и др.
в: Journal of Fluorine Chemistry, Том 280, 110371, 11.2024.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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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