Anti-influenza activity of diazaadamantanes combined with monoterpene moieties

Evgeniy Suslov, Vladimir V. Zarubaev, Alexander V. Slita, Konstantin Ponomarev, Dina Korchagina, Daniel M. Ayine-Tora, Jóhannes Reynisson, Konstantin Volcho, Nariman Salakhutdinov

Результат исследования: Научные публикации в периодических изданияхстатья

7 Цитирования (Scopus)

Аннотация

The antiviral activity of several diaza-adamantanes containing monoterpenoid moieties against a rimantadine-resistant strain of the influenza A/Puerto Rico/8/34 (H1N1) virus was studied. Hetero-adamantanes containing monoterpene moieties at the aminal position of the heterocycle were found to exhibit lower activity compared to compounds with a diaza-adamantane fragment and a monoterpene moiety linked via an amino group at the 6-position of the hetero-adamantane ring. The highest selectivity index (a ratio of the 50% cytotoxic concentration to the 50% inhibitory concentration) out of 30 was observed for compound 8d, which contains a citronellal monoterpenoid moiety. Diaza-adamantane 8d was superior to its adamantane-containing analog 5 both in its anti-influenza activity and selectivity. Furthermore, 8d has more balanced physicochemical properties than 5, making the former a more promising drug candidate. Modelling these compounds against an influenza virus M2 ion channel predicted plausible binding modes to both the wild-type and the mutant (S31N).

Язык оригиналаанглийский
Страницы (с-по)4531-4535
Число страниц5
ЖурналBioorganic and Medicinal Chemistry Letters
Том27
Номер выпуска19
DOI
СостояниеОпубликовано - 1 окт 2017

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  • Цитировать

    Suslov, E., Zarubaev, V. V., Slita, A. V., Ponomarev, K., Korchagina, D., Ayine-Tora, D. M., Reynisson, J., Volcho, K., & Salakhutdinov, N. (2017). Anti-influenza activity of diazaadamantanes combined with monoterpene moieties. Bioorganic and Medicinal Chemistry Letters, 27(19), 4531-4535. https://doi.org/10.1016/j.bmcl.2017.08.062