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

Elisabeth Greiner, Arthur J. Atkinson, Alejandro R 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 Citations (Scopus)

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

Fingerprint

Pharmacokinetics
Amines
Carbon
Substrates
antalarmin
7H-pyrrolo(2,3-d)pyrimidin-4-amine

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

Cite this

Greiner, E., Atkinson, A. J., Ayala, A. R., Chrousos, G. P., Contoreggi, C., Eckelman, W. C., ... 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

Synthesis of doubly 13C-labelled antalarmin isotopomers for pharmacokinetic studies. / Greiner, Elisabeth; Atkinson, Arthur J.; Ayala, Alejandro R; Chrousos, George P.; Contoreggi, Carlo; Eckelman, William C.; Gold, Philip W.; Habib, Kamal E.; Jacobson, Arthur E.; Whittaker, Noel; Webster, Elizabeth L.; Rice, Kenner C.

In: Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 45, No. 8, 14.08.2002, p. 637-645.

Research output: Contribution to journalArticle

Greiner, E, Atkinson, AJ, Ayala, AR, Chrousos, GP, Contoreggi, C, Eckelman, WC, Gold, PW, Habib, KE, Jacobson, AE, Whittaker, N, Webster, EL & Rice, KC 2002, 'Synthesis of doubly 13C-labelled antalarmin isotopomers for pharmacokinetic studies', Journal of Labelled Compounds and Radiopharmaceuticals, vol. 45, no. 8, pp. 637-645. https://doi.org/10.1002/jlcr.576
Greiner, Elisabeth ; Atkinson, Arthur J. ; Ayala, Alejandro R ; Chrousos, George P. ; Contoreggi, Carlo ; Eckelman, William C. ; Gold, Philip W. ; Habib, Kamal E. ; Jacobson, Arthur E. ; Whittaker, Noel ; Webster, Elizabeth L. ; Rice, Kenner C. / Synthesis of doubly 13C-labelled antalarmin isotopomers for pharmacokinetic studies. In: Journal of Labelled Compounds and Radiopharmaceuticals. 2002 ; Vol. 45, No. 8. pp. 637-645.
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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).",
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AU - Gold, Philip W.

AU - Habib, Kamal E.

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