Synthesis of doubly 13C-labelled antalarmin isotopomers for pharmacokinetic studies

Elisabeth Greiner, Arthur J. Atkinson, Alejandro Ayala, George P. Chrousos, Carlo Contoreggi, William C. Eckelman, Philip W. Gold, Kamal E. Habib, Arthur E. Jacobson, Noel Whittaker, Elizabeth L. Webster, Kenner C. Rice

Research output: Contribution to journalArticle

3 Scopus citations

Abstract

Antalarmin (butyl-ethyl-[2,5,6-trimethyl-7-(2,4,6-trimethyl-phenyl)-7H-pyrro-lo[2, 3-d]pyrimidin-4-yl]-amine) was doubly labelled with carbon-13. The synthesized butyl-[13C2]ethyl-[2,5,6-trimethyl-7-(2,4, 6-trimethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine (1) and butyl-ethyl-[2-13C]-[2,5,6-trimethyl-7-(2,4, 6-trimethyl-phenyl)-7H-pyrrolo[2,3-d]-[2-13C] pyrimidin-4-yl]- amine, (2) were prepared for use as substrates for pharmacokinetic studies. These compounds were obtained in fair overall yield in a 5 and 6 step synthesis (20-24.5%, respectively) and high isotopic purity (about 99 at% 13C).

Original languageEnglish (US)
Pages (from-to)637-645
Number of pages9
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume45
Issue number8
DOIs
StatePublished - Aug 14 2002
Externally publishedYes

Keywords

  • Antalarmin
  • Carbon-13 labelling
  • Corticotropin-releasing hormone
  • CRHR1 antagonist

ASJC Scopus subject areas

  • Analytical Chemistry
  • Drug Discovery
  • Organic Chemistry
  • Clinical Biochemistry
  • Molecular Medicine
  • Pharmacology

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  • Cite this

    Greiner, E., Atkinson, A. J., Ayala, A., Chrousos, G. P., Contoreggi, C., Eckelman, W. C., Gold, P. W., Habib, K. E., Jacobson, A. E., Whittaker, N., Webster, E. L., & Rice, K. C. (2002). Synthesis of doubly 13C-labelled antalarmin isotopomers for pharmacokinetic studies. Journal of Labelled Compounds and Radiopharmaceuticals, 45(8), 637-645. https://doi.org/10.1002/jlcr.576