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Allosteric agonists of the calcium receptor (CaR): fluorine and SF5 analogues of cinacalcet

Chia, Poh Wai, Brennan, Sarah C. ORCID: https://orcid.org/0000-0002-8719-4367, Slawin, Alexandra M. Z., Riccardi, Daniela ORCID: https://orcid.org/0000-0002-7322-3163 and O'Hagan, David 2012. Allosteric agonists of the calcium receptor (CaR): fluorine and SF5 analogues of cinacalcet. Organic & Biomolecular Chemistry 10 (39) , pp. 7922-7927. 10.1039/c2ob26402a

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Abstract

Three selectively fluorinated cinacalcet analogues are prepared and their activity as calcium-sensing receptor (CaR) agonists is assessed. Individual (2R,1′R)-2 and (2S,1′R)-3 fluorocinacalcet diastereoisomers were prepared using the MacMillan asymmetric fluorination reaction. Assays with the recombinant human CaR revealed that both diastereoisomers have a similar potency to each other although slightly lower (75–80%) than that of cinacalcet 1. The SF5-cinacalcet analogue 4 was prepared from meta-pentafluorosulfanyl benzyl alcohol and has [similar]75% agonist activity relative to cinacalcet 1 indicating that the SF5 group can replace the CF3 group and retain significant bioactivity.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Biosciences
Subjects: Q Science > QD Chemistry
Publisher: Royal Society of Chemistry
ISSN: 1477-0520
Last Modified: 25 Oct 2022 09:03
URI: https://orca.cardiff.ac.uk/id/eprint/57008

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