Bioorganic and Medicinal Chemistry Letters p. 4531 - 4535 (2017)
Update date:2022-08-29
Topics:
Suslov, Evgeniy
Zarubaev, Vladimir V.
Slita, Alexander V.
Ponomarev, Konstantin
Korchagina, Dina
Ayine-Tora, Daniel M.
Reynisson, Jóhannes
Volcho, Konstantin
Salakhutdinov, Nariman
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).
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TIANJIN GST CHEMICAL TECHNOLOGY CO., LTD
Contact:+86-22-25210964
Address:Room. 208, No. -12-C, No. 13, Xinbei Road, Tanggu District, New Haixin Area, Tianjin City, China
Doi:10.1016/0022-328X(86)80050-X
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