Anti-influenza activity of diazaadamantanes combined with monoterpene moieties.

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dc.contributor.author Suslov, Evgeniy en
dc.contributor.author Zarubaev, Vladimir V en
dc.contributor.author Slita, Alexander V en
dc.contributor.author Ponomarev, Konstantin en
dc.contributor.author Korchagina, Dina en
dc.contributor.author Ayine-Tora, Daniel en
dc.contributor.author Reynisson, Johannes en
dc.contributor.author Volcho, Konstantin en
dc.contributor.author Salakhutdinov, Nariman en
dc.date.accessioned 2018-11-07T21:37:23Z en
dc.date.issued 2017-10 en
dc.identifier.issn 0960-894X en
dc.identifier.uri http://hdl.handle.net/2292/44079 en
dc.description.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). en
dc.format.medium Print-Electronic en
dc.language eng en
dc.relation.ispartofseries Bioorganic & Medicinal Chemistry Letters en
dc.rights Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. en
dc.rights.uri https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.subject Aza Compounds en
dc.subject Adamantane en
dc.subject Monoterpenes en
dc.subject Antiviral Agents en
dc.subject Microbial Sensitivity Tests en
dc.subject Molecular Structure en
dc.subject Structure-Activity Relationship en
dc.subject Dose-Response Relationship, Drug en
dc.subject Influenza A Virus, H1N1 Subtype en
dc.title Anti-influenza activity of diazaadamantanes combined with monoterpene moieties. en
dc.type Journal Article en
dc.identifier.doi 10.1016/j.bmcl.2017.08.062 en
pubs.issue 19 en
pubs.begin-page 4531 en
pubs.volume 27 en
dc.rights.holder Copyright: The author en
dc.identifier.pmid 28886889 en
pubs.end-page 4535 en
pubs.publication-status Published en
dc.rights.accessrights http://purl.org/eprint/accessRights/RestrictedAccess en
pubs.subtype Research Support, Non-U.S. Gov't en
pubs.subtype Journal Article en
pubs.elements-id 668606 en
pubs.org-id Libraries & Learning Services en
pubs.org-id Libraries & Learning Services en
pubs.org-id Research and Collections en
pubs.org-id Research and Collections en
pubs.org-id Collection Development and Access en
pubs.org-id Collection Development and Access en
pubs.org-id Science en
pubs.org-id Science Research en
pubs.org-id Maurice Wilkins Centre (2010-2014) en
dc.identifier.eissn 1464-3405 en
pubs.record-created-at-source-date 2017-09-10 en
pubs.dimensions-id 28886889 en


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