Efficient synthesis of novel fluorinated phenanthridin-6(5H)-one derivatives and in vitro evaluation of their antiviral activity

Efficient synthesis of novel fluorinated phenanthridin-6(5H)-one derivatives and in vitro evaluation of their antiviral activity Научная публикация

Журнал

Journal of Fluorine Chemistry
ISSN: 0022-1139

Вых. Данные

Год: 2024, Том: 274, Страницы: 110240 Страниц : 1 DOI: 10.1016/j.jfluchem.2024.110240

Ключевые слова

Fluorinated 2-amino-1,1′-biphenyls; Aryl isocyanates; Trifluoromethanesulfonic acid; Influenza virus

Авторы

Gurskaya Larisa ¹ , Politanskaya Larisa ¹ , Wang Jiaying ^1,2 , Ilyina Polina ³ , Volobueva Alexandrina ³ , Zarubaev Vladimir ³

Организации

1	Siberian Branch of Russian Academy of Sciences, Vorozhtsov Novosibirsk Institute of Organic Chemistry, Ac. Lavrentiev Ave., 9, Novosibirsk 630090, Russian Federation
2	Novosibirsk State University, Pirogova Street, 2, Novosibirsk 630090, Russian Federation
3	Saint-Petersburg Pasteur Research Institute of Epidemiology and Microbiology, Mira Street, 14, Saint-Petersburg 197101, Russian Federation

Highlights • A series of isomeric fluorinated phenanthridin-6(5H)-one derivatives was synthesized for the first time. • The key stage of synthesis was simplified compared to previous methods. • Phenanthridin-6(5H)-one showed no antiviral activity, but its 2-fluoro-substituted derivative had the influenza virus inhibition properties. Abstract A convenient and efficient method for the synthesis of fluorinated phenanthridin-6(5H)-ones from the corresponding 2-isocyanato-1,1′-biphenyls mediated by trifluoromethanesulfonic acid in chlorobenzene is described. The reaction uses readily available starting materials, takes place under very mild reaction conditions (r. t.) and provides access to biologically promising fluorinated heterocycles in good to excellent yields. Synthesized compounds were tested in vitro for cytotoxicity in MDCK cell line and for antiviral activity against influenza virus A/Puerto Rico/8/34 (H1N1).

Gurskaya L. , Politanskaya L. , Wang J. , Ilyina P. , Volobueva A. , Zarubaev V.
Efficient synthesis of novel fluorinated phenanthridin-6(5H)-one derivatives and in vitro evaluation of their antiviral activity
Journal of Fluorine Chemistry. 2024. V.274. P.110240. DOI: 10.1016/j.jfluchem.2024.110240 WOS

Поступила в редакцию:	2 дек. 2023 г.
Принята к публикации:	2 янв. 2024 г.
Опубликована online:	6 янв. 2024 г.

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