Influenza antiviral activity of F- and OH-containing isopulegol-derived octahydro-2H-chromenes

Influenza antiviral activity of F- and OH-containing isopulegol-derived octahydro-2H-chromenes Full article

Journal

Bioorganic and Medicinal Chemistry Letters
ISSN: 0960-894X , E-ISSN: 1464-3405

Output data

Year: 2021, Volume: 31, Article number : 127677, Pages count : DOI: 10.1016/j.bmcl.2020.127677

Tags

Antiviral; Chromene; Fluorine; Influenza; Monoterpene

Authors

Ilyina I.V. ¹ , Patrusheva O.S. ¹ , Zarubaev V.V. ² , Misiurina Maria A. ² , Slita A.V. ² , Esaulkova I.L. ² , Korchagina D.V. ¹ , Gatilov Y.V. ¹ , Borisevich S.S. ³ , Volcho K.P. ¹ , Salakhutdinov N.F. ¹

Affiliations

1	(Scopus) Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrentjev av.9, Novosibirsk, 630090, Russian Federation
2	(Scopus) Pasteur Institute of Epidemiology and Microbiology, 14 Mira str., St. Petersburg, 197101, Russian Federation
3	(Scopus) Laboratory of Chemical Physics, Ufa Chemistry Institute of the Ufa Federal Research Center, 71 Octyabrya pr., Ufa, 450054, Russian Federation

We synthesized fluoro- and hydroxy-containing octahydro-2H-chromenes by the Prins reaction starting from a monoterpenoid (–)-isopulegol and a wide range of aromatic aldehydes in the presence of the BF3∙Et2O/H2O system acting as both an acid catalyst and a fluorine source. Activity of the produced compounds against the influenza A/Puerto Rico/8/34 (H1N1) virus was studied. The highest activity was demonstrated by fluoro- (11i) and hydroxy-containing (10i) derivatives of 2,4,6-trimethoxybenzaldehyde. The most pronounced virus-inhibiting effect of compounds 10i and 11i was observed at an early stage of infection. These compounds were supposed to be capable of binding to viral hemagglutinin, which is an agreement with data on the effect of compounds 10i and 11i on the viral fusogenic activity as well as by molecular docking studies. © 2020

Ilyina I.V. , Patrusheva O.S. , Zarubaev V.V. , Misiurina M.A. , Slita A.V. , Esaulkova I.L. , Korchagina D.V. , Gatilov Y.V. , Borisevich S.S. , Volcho K.P. , Salakhutdinov N.F.
Influenza antiviral activity of F- and OH-containing isopulegol-derived octahydro-2H-chromenes
Bioorganic and Medicinal Chemistry Letters. 2021. V.31. 127677 . DOI: 10.1016/j.bmcl.2020.127677 WOS Scopus РИНЦ

Published print:

Jan 1, 2021

Web of science	WOS:000602367900010
Scopus	2-s2.0-85096012979
Elibrary	45149413
OpenAlex	W3095361890