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dc.contributor.author
Schneider, Petra
dc.contributor.author
Schneider, Gisbert
dc.date.accessioned
2017-12-14T10:37:00Z
dc.date.available
2017-10-06T02:11:25Z
dc.date.available
2017-12-13T14:56:23Z
dc.date.available
2017-12-14T10:37:00Z
dc.date.issued
2017-06-26
dc.identifier.issn
1433-7851
dc.identifier.issn
1521-3773
dc.identifier.issn
0570-0833
dc.identifier.other
10.1002/anie.201702816
en_US
dc.identifier.uri
http://hdl.handle.net/20.500.11850/190528
dc.identifier.doi
10.3929/ethz-b-000190528
dc.description.abstract
Privileged structures inspire compound library design in medicinal chemistry. We performed a comprehensive analysis of 1.4 million bioactive compounds, with the aim of assessing the prevalence of certain molecular frameworks. We used the Shannon entropy formalism to quantify the promiscuity of the most frequently observed atom scaffolds across the annotated target families. This analysis revealed an apparent inverse relationship between hydrogen-bond-acceptor count of a scaffold and its potential promiscuity. The results further suggest that chemically easily accessible scaffolds can serve as templates for the generation of bespoke compound libraries with differing degrees of multiple target engagement, and heterocyclic, sp3-rich frameworks are particularly suited for target-focused library design. The outcome of our study enables us to place some of the many narratives surrounding the concept of privileged structures into a critical context.
en_US
dc.language.iso
en
en_US
dc.publisher
Wiley
en_US
dc.rights.uri
http://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subject
cheminformatics
en_US
dc.subject
Shannon entropy
en_US
dc.subject
combinatorial chemistry
en_US
dc.subject
polypharmacology
en_US
dc.subject
medicinal chemistry
en_US
dc.title
Privileged Structures Revisited
en_US
dc.type
Journal Article
dc.rights.license
Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International
dc.date.published
2017-05-30
ethz.journal.title
Angewandte Chemie. International Edition
ethz.journal.volume
56
en_US
ethz.journal.issue
27
en_US
ethz.journal.abbreviated
Angew. Chem. Int. Ed.
ethz.pages.start
7971
en_US
ethz.pages.end
7974
en_US
ethz.version.deposit
publishedVersion
en_US
ethz.identifier.wos
ethz.publication.place
Weinheim
en_US
ethz.publication.status
published
en_US
ethz.leitzahl
ETH Zürich::00002 - ETH Zürich::00012 - Lehre und Forschung::00007 - Departemente::02020 - Dep. Chemie und Angewandte Biowiss. / Dep. of Chemistry and Applied Biosc.::02534 - Institut für Pharmazeutische Wiss. / Institute of Pharmaceutical Sciences::03852 - Schneider, Gisbert / Schneider, Gisbert
en_US
ethz.leitzahl.certified
ETH Zürich::00002 - ETH Zürich::00012 - Lehre und Forschung::00007 - Departemente::02020 - Dep. Chemie und Angewandte Biowiss. / Dep. of Chemistry and Applied Biosc.::02534 - Institut für Pharmazeutische Wiss. / Institute of Pharmaceutical Sciences::03852 - Schneider, Gisbert / Schneider, Gisbert
en_US
ethz.date.deposited
2017-10-06T02:11:39Z
ethz.source
WOS
ethz.eth
yes
en_US
ethz.availability
Open access
en_US
ethz.rosetta.installDate
2017-12-13T14:56:25Z
ethz.rosetta.lastUpdated
2018-11-06T05:34:53Z
ethz.rosetta.exportRequired
true
ethz.rosetta.versionExported
true
ethz.COinS
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