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Direct syntheses of stereoisomers of 3-fluoro GABA and β-fluoroamine analogues of the calcium receptor (CaR) agonists, cinacalcet, tecalcet, fendilines and NPS R-467
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dc.contributor.author | Renault, Yohann J. G. | |
dc.contributor.author | Diao, Jiayin | |
dc.contributor.author | Cordes, David B. | |
dc.contributor.author | Leach, Katie | |
dc.contributor.author | O'Hagan, David | |
dc.date.accessioned | 2023-07-25T08:30:22Z | |
dc.date.available | 2023-07-25T08:30:22Z | |
dc.date.issued | 2023-07-24 | |
dc.identifier | 290321372 | |
dc.identifier | 3d84c7c3-7974-4be2-92ce-c094e89a2c5f | |
dc.identifier | 85165515055 | |
dc.identifier.citation | Renault , Y J G , Diao , J , Cordes , D B , Leach , K & O'Hagan , D 2023 , ' Direct syntheses of stereoisomers of 3-fluoro GABA and β-fluoroamine analogues of the calcium receptor (CaR) agonists, cinacalcet, tecalcet, fendilines and NPS R-467 ' , Medicinal Chemistry Research , vol. 32 , pp. 1532-1542 . https://doi.org/10.1007/s00044-023-03103-0 | en |
dc.identifier.issn | 1054-2523 | |
dc.identifier.other | ORCID: /0000-0002-0510-5552/work/139552080 | |
dc.identifier.other | ORCID: /0000-0002-5366-9168/work/139554074 | |
dc.identifier.uri | https://hdl.handle.net/10023/28018 | |
dc.description.abstract | Synthetic routes following a sequential MacMillan organocatalytic asymmetric α-fluorination protocol for aldehydes and then reductive amination, have allowed ready access to bioactive β-fluoroamines. The approach is demonstrated with a short synthesis of (S)-3-fluoro-γ-aminobutyric acid (3F-GABA) and was extended to β-fluoroamine stereoisomers of cinacalcet, tecalcet, fendiline and NPS R-467, all allosteric modulators of the calcium receptor (CaR). Stereoisomers of the fluorinated calcimimetic analogues were then assayed in a CaR receptor assay and a comparison of β-fluoroamine matched pair stereoisomers revealed a binding mode preference to the receptor as deduced from conformations which will be favoured as a consequence of the electrostatic gauche effect. | |
dc.format.extent | 11 | |
dc.format.extent | 1085623 | |
dc.language.iso | eng | |
dc.relation.ispartof | Medicinal Chemistry Research | en |
dc.subject | Electrostatic gauche effect | en |
dc.subject | Calimimetics | en |
dc.subject | Cinacalcet | en |
dc.subject | Fluorinated drugs | en |
dc.subject | Calcium receptors | en |
dc.subject | Asymmetric fluorination | en |
dc.subject | QD Chemistry | en |
dc.subject | RR-NDAS | en |
dc.subject | MCC | en |
dc.subject.lcc | QD | en |
dc.title | Direct syntheses of stereoisomers of 3-fluoro GABA and β-fluoroamine analogues of the calcium receptor (CaR) agonists, cinacalcet, tecalcet, fendilines and NPS R-467 | en |
dc.type | Journal article | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.contributor.institution | University of St Andrews. Institute of Behavioural and Neural Sciences | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.identifier.doi | 10.1007/s00044-023-03103-0 | |
dc.description.status | Peer reviewed | en |
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