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Janus all-cis 2,3,4,5,6-pentafluorocyclohexyl building blocks applied to medicinal chemistry and bioactives discovery chemistry
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dc.contributor.author | Clark, Joshua | |
dc.contributor.author | Neyyappadath, Rifahath M. | |
dc.contributor.author | Yu, Cihang | |
dc.contributor.author | Slawin, Alexandra M. Z. | |
dc.contributor.author | Cordes, David B. | |
dc.contributor.author | O'Hagan, David | |
dc.date.accessioned | 2021-10-06T14:30:06Z | |
dc.date.available | 2021-10-06T14:30:06Z | |
dc.date.issued | 2021-11-17 | |
dc.identifier | 275759219 | |
dc.identifier | 3eb00041-ec0a-4aa9-823b-4397ad369478 | |
dc.identifier | 85116415558 | |
dc.identifier | 000703997000001 | |
dc.identifier.citation | Clark , J , Neyyappadath , R M , Yu , C , Slawin , A M Z , Cordes , D B & O'Hagan , D 2021 , ' Janus all- cis 2,3,4,5,6-pentafluorocyclohexyl building blocks applied to medicinal chemistry and bioactives discovery chemistry ' , Chemistry - A European Journal , vol. 27 , no. 64 , 202102819 , pp. 16000-16005 . https://doi.org/10.1002/chem.202102819 | en |
dc.identifier.issn | 0947-6539 | |
dc.identifier.other | RIS: urn:222867F1684BC4E4C2572CF96C419D0D | |
dc.identifier.other | ORCID: /0000-0002-0510-5552/work/101217835 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/101217853 | |
dc.identifier.other | ORCID: /0000-0002-5366-9168/work/101217884 | |
dc.identifier.uri | https://hdl.handle.net/10023/24093 | |
dc.description | We thank EPSRC for a grant (EP/R013799/1) and Studentships (JLC) through the EPSRC CRITICAT CDT programme and also the Chinese Scholarship Council (CY). | en |
dc.description.abstract | Monoalkylated derivatives of the unusually polar all- cis 2,3,4,5,6- pentafluorocyclohexyl (Janus face) motif are prepared starting from an aryl hydrogenation of 2,3,4,5,6- pentafluorophenylacetate methyl ester 15 . The method used Zeng's Rh(CAAC) carbene catalyst 4 in the hydrogenation following the protocol developed by Glorius. The resultant Janus pentafluorocyclohexylacetate methyl ester 16 was converted to the corresponding alcohol 18 , aldehyde 13 , bromide 29 and azide 14 through functional group manipulations, and some of these building blocks were used in Ugi-multicomponent and Cu-catalysed click reactions. NBoc protected pentafluoroarylphenylalanine methyl ester 35 was also subject to an aryl hydrogenation, and then deprotection to generate the Janus face ß-pentafluorocyclohexyl-alanine amino acid 15 , which was incorporated into representative members of an emerging class of candidate antiviral compounds. Log P measurements demonstrate that the all- cis 2,3,4,5,6-pentafluorocyclohexyl ring system is more polar than a phenyl ring. In overview the paper introduces new building blocks containing this Janus ring and demonstrates their progression to molecules typically used in bioactives discovery programmes. | |
dc.format.extent | 7 | |
dc.format.extent | 4715623 | |
dc.language.iso | eng | |
dc.relation.ispartof | Chemistry - A European Journal | en |
dc.subject | Organofluorine chemistry | en |
dc.subject | Janus motif | en |
dc.subject | Aryl hydrogenation | en |
dc.subject | Organic chemistry | en |
dc.subject | Fluorocyclohexanes | en |
dc.subject | QD Chemistry | en |
dc.subject | QH301 Biology | en |
dc.subject | R Medicine | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.subject.lcc | QH301 | en |
dc.subject.lcc | R | en |
dc.title | Janus all-cis 2,3,4,5,6-pentafluorocyclohexyl building blocks applied to medicinal chemistry and bioactives discovery chemistry | en |
dc.type | Journal article | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | 10.1002/chem.202102819 | |
dc.description.status | Peer reviewed | en |
dc.identifier.grantnumber | EP/R013799/1 | en |
dc.identifier.grantnumber | EP/L016419/1 | en |
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