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Title: Anti-influenza activity of diazaadamantanes combined with monoterpene moieties
Authors: Suslov, Evgeniy
Ponomarev, Konstantin
Korchagina, Dina
Ayine-Tora, Daniel M
Reynisson, Jóhannes
Volcho, Konstantin
Salakhutdinov, Nariman
Zarubaev, Vladimir V. 
Slita, Alexander V. 
Keywords: Antivirals;Citronellal;Diaza-adamantane;Influenza;Myrtenal;Terpene
Issue Date: 2017
Publisher: Elsevier
Journal: Bioorganic and Medicinal Chemistry Letters 
Abstract: 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).
ISSN: 0960-894X
DOI: 10.1016/j.bmcl.2017.08.062
Appears in Collections:Journal articles

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