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Metabolism and hydrophilicity of the polarised ‘Janus face’ all-cis tetrafluorocyclohexyl ring, a candidate motif for drug discovery

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Slawin_2018_CS_MetabolismJanusFace_CCBY_VoR.pdf (568.6Kb)
Date
21/03/2018
Author
Rodil, Andrea
Bosisio, Stefano
Salah Ayoup, Mohammed
Quinn, Laura
Cordes, David B.
Slawin, Alexandra M. Z.
Murphy, Cormac
Michel, Julien
O'Hagan, David
Funder
European Commission
Grant ID
607787
Keywords
QD Chemistry
NDAS
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Abstract
The metabolism and polarity of the all-cis tetra-fluorocyclohexane motif is explored in the context of its potential as a motif for inclusion in drug discovery programmes. Biotransformations of phenyl all-cis tetra-, tri- and di- fluoro cyclohexanes with the human metabolism model organism Cunninghamella elegans illustrates various hydroxylated products, but limited to benzylic hydroxylation for the phenyl all-cis tetrafluorocyclohexyl ring system. Evaluation of the lipophilicities (Log P) indicate a significant and progressive increase in polarity with increasing fluorination on the cyclohexane ring system. Molecular dynamics simulations indicate that water associates much more closely with the hydrogen face of these Janus face cyclohexyl rings than the fluorine face owing to enhanced hydrogen bonding interactions with the polarised hydrogens and water.
Citation
Rodil , A , Bosisio , S , Salah Ayoup , M , Quinn , L , Cordes , D B , Slawin , A M Z , Murphy , C , Michel , J & O'Hagan , D 2018 , ' Metabolism and hydrophilicity of the polarised ‘Janus face’ all- cis tetrafluorocyclohexyl ring, a candidate motif for drug discovery ' , Chemical Science , vol. 9 , no. 11 , pp. 3023-3028 . https://doi.org/10.1039/C8SC00299A
Publication
Chemical Science
Status
Peer reviewed
DOI
https://doi.org/10.1039/C8SC00299A
ISSN
2041-6520
Type
Journal article
Rights
Copyright 2018 the Authors. This is an Open Access Article licensed under a Creative Commons Attribution 3.0 Unported Licence
Description
This work was supported by the Initial Training Network, FLUOR21, funded by the FP7 Marie Curie Actions of the European Commission (FP7-PEOPLE-2013-ITN-607787). JM is supported by a University Research Fellowship from the Royal Society. The research leading to these results has received funding from the European Research Council under the EU 7th Framework Programme (FP7/2007-2013)/ERC No 336289.
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  • University of St Andrews Research
URL
http://www.rsc.org/suppdata/c8/sc/c8sc00299a/c8sc00299a1.pdf
URI
http://hdl.handle.net/10023/12800

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