title: Anti-influenza activity of monoterpene-derived substituted hexahydro-2H-chromenes.
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.
authors: Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 630090 Novosibirsk, Russia.
authors: Oksana S
authors: OS
authors: Patrusheva
authors: Department of Chemotherapy, Influenza Research Institute, 15/17 Prof. Popova St., 197376 St. Petersburg, Russia. Electronic address: vladimir.zarubaev@influenza.spb.ru.
authors: Vladimir V
authors: VV
authors: Zarubaev
authors: Department of Chemotherapy, Influenza Research Institute, 15/17 Prof. Popova St., 197376 St. Petersburg, Russia.
authors: Anna A
authors: AA
authors: Shtro
authors: Department of Chemotherapy, Influenza Research Institute, 15/17 Prof. Popova St., 197376 St. Petersburg, Russia.
authors: Yana R
authors: YR
authors: Orshanskaya
authors: Department of Chemotherapy, Influenza Research Institute, 15/17 Prof. Popova St., 197376 St. Petersburg, Russia.
authors: Sergey A
authors: SA
authors: Boldyrev
authors: Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 630090 Novosibirsk, Russia; Novosibirsk State University, Pirogova 2, Novosibirsk 630090, Russia.
authors: Irina V
authors: IV
authors: Ilyina
authors: Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 630090 Novosibirsk, Russia.
authors: Svetlana Yu
authors: SY
authors: Kurbakova
authors: Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 630090 Novosibirsk, Russia.
authors: Dina V
authors: DV
authors: Korchagina
authors: Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 630090 Novosibirsk, Russia; Novosibirsk State University, Pirogova 2, Novosibirsk 630090, Russia.
authors: Konstantin P
authors: KP
authors: Volcho
authors: Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 630090 Novosibirsk, Russia; Novosibirsk State University, Pirogova 2, Novosibirsk 630090, Russia.
authors: Nariman F
authors: NF
authors: Salakhutdinov
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001578:Benzopyrans / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D006801:Humans; D009980:Influenza A virus / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D039821:Monoterpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000998:Antiviral Agents; D001578:Benzopyrans; D039821:Monoterpenes
keywords: Antiviral; Chromene; Influenza; Monoterpene