1402230-83-4Relevant articles and documents
Allosteric agonists of the calcium receptor (CaR): Fluorine and SF 5 analogues of cinacalcet
Chia, Poh Wai,Brennan, Sarah C.,Slawin, Alexandra M. Z.,Riccardi, Daniela,O'Hagan, David
, p. 7922 - 7927 (2013/07/05)
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 ~75% agonist activity relative to cinacalcet 1 indicating that the SF5 group can replace the CF3 group and retain significant bioactivity.