Anti-influenza activity of monoterpene-derived substituted hexahydro-2H-chromenes

Bioorg Med Chem. 2016 Nov 1;24(21):5158-5161. doi: 10.1016/j.bmc.2016.08.037.

Oksana S Patrusheva ¹, Vladimir V Zarubaev ², Anna A Shtro ³, Yana R Orshanskaya ³, Sergey A Boldyrev ³, Irina V Ilyina ⁴, Svetlana Yu Kurbakova ¹, Dina V Korchagina ¹, Konstantin P Volcho ⁴, Nariman F Salakhutdinov ⁴

Affiliations

1 Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 630090 Novosibirsk, Russia.
2 Department of Chemotherapy, Influenza Research Institute, 15/17 Prof. Popova St., 197376 St. Petersburg, Russia. Electronic address: vladimir.zarubaev@influenza.spb.ru.
3 Department of Chemotherapy, Influenza Research Institute, 15/17 Prof. Popova St., 197376 St. Petersburg, Russia.
4 Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 630090 Novosibirsk, Russia; Novosibirsk State University, Pirogova 2, Novosibirsk 630090, Russia.

PMID: 27591012 DOI: 10.1016/j.bmc.2016.08.037

Abstract

The Antiviral activity of 4-hydroxy-hexahydro-2H-chromenes and 4-fluorine-hexahydro-2H-chromenes with an aromatic substituent, synthesized from monoterpene (-)-verbenone, was studied for the first time. Five of 11 (45 per cent) of 4-hydroxy-hexahydro-2H-chromene-type compounds have been found to exhibit Antiviral activity against influenza A virus of subtype H1N1pdm09. Although a portion of active compounds among 4-fluorine-containing series was fewer, just compound 5i that contains a fluorine substituent exhibited more potent anti-influenza activity along with low cytotoxicity. Thus two new promising types of Antiviral compounds were identified.

Keywords

Antiviral; Chromene; Influenza; Monoterpene.

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