Synthesis of the calcilytic ligand NPS 2143

Henrik Johansson, Thomas Cailly, Alex Rojas Bie Thomsen, Hans Bräuner-Osborne, Daniel Sejer Pedersen

Research output: Contribution to journalArticlepeer-review

Abstract

(R)-3 (NPS 2143) is a negative allosteric modulator of the human calcium-sensing receptor (CaSR) and as such represents an important pharmacological tool compound for studying the CaSR. Herein, we disclose for the first time a complete experimental description, detailed characterisation and assessment of enantiomeric purity for (R)-3. An efficient, reproducible and scalable synthesis of (R)-3 that requires a minimum of chromatographic purification steps is presented. (R)-3 was obtained in excellent optical purity (er > 99:1) as demonstrated by chiral HPLC and the pharmacological profile for (R)-3 is in full accordance with that reported in the literature.

Original languageEnglish (US)
Pages (from-to)1383-1387
Number of pages5
JournalBeilstein Journal of Organic Chemistry
Volume9
DOIs
StatePublished - Jul 9 2013

Keywords

  • Epoxides
  • GPCR
  • NPS 2143
  • Nucleophilic aromatic substitution
  • Pyrylium chemistry

ASJC Scopus subject areas

  • Organic Chemistry

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