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

Bioorg Med Chem Lett. 2021 Jan 1:31:127677. doi: 10.1016/j.bmcl.2020.127677.

Irina V Ilyina ¹, Oksana S Patrusheva ¹, Vladimir V Zarubaev ², Maria A Misiurina ², Alexander V Slita ², Iana L Esaulkova ², Dina V Korchagina ¹, Yuri V Gatilov ¹, Sophia S Borisevich ³, Konstantin P Volcho ⁴, Nariman F Salakhutdinov ¹

Affiliations

1 Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrentjev av.9, 630090 Novosibirsk, Russia.
2 Pasteur Institute of Epidemiology and Microbiology, 14 Mira str., 197101 St. Petersburg, Russia.
3 Laboratory of Chemical Physics, Ufa Chemistry Institute of the Ufa Federal Research Center, 71 Octyabrya pr., 450054 Ufa, Russia.
4 Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrentjev av.9, 630090 Novosibirsk, Russia. Electronic address: volcho@nioch.nsc.ru.

PMID: 33171219 DOI: 10.1016/j.bmcl.2020.127677

Abstract

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.

Keywords

Antiviral; Chromene; Fluorine; Influenza; Monoterpene.

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