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 Full article

Journal

Journal of Fluorine Chemistry
ISSN: 0022-1139

Output data

Year: 2024, Volume: 274, Pages: 110240 Pages count : 1 DOI: 10.1016/j.jfluchem.2024.110240

Tags

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

Authors

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

Affiliations

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

Submitted:	Dec 2, 2023
Accepted:	Jan 2, 2024
Published online:	Jan 6, 2024

Web of science	WOS:001155807600001
OpenAlex	W4390645293