A new facile synthetic route to [11C]GSK189254, a selective PET radioligand for imaging of CNS histamine H3 receptor

Min Wang, Mingzhang Gao, Brandon L. Steele, Barbara E. Glick-Wilson, Clive Brown-Proctor, Anantha Shekhar, Gary Hutchins, Qi-Huang Zheng

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

GSK189254 and its corresponding precursor GSK185071B were synthesized from 3-methoxyphenylacetic acid with 6-chloropyridine-3-carbolic acid or 6-chloronicotinamide in 8 and 7 steps with either 6% or 7% and either 14% or 16% yield, respectively. [11C]GSK189254 was prepared from GSK185071B with [11C]CH3OTf through N-[11C]methylation and isolated by HPLC combined with solid-phase extraction (SPE) in 50-60% radiochemical yield based on [11C]CO2 and decay corrected to end of bombardment (EOB), with 370-740 GBq/μmol specific activity at EOB.

Original languageEnglish
Pages (from-to)4713-4718
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume22
Issue number14
DOIs
StatePublished - Jul 15 2012

Fingerprint

Histamine H3 Receptors
Imaging techniques
Methylation
Solid Phase Extraction
Phenol
High Pressure Liquid Chromatography
6-((3-cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy)-N-methyl-3-pyridinecarboxamide
3-methoxyphenylacetic acid

Keywords

  • [C]GSK189254
  • Automation
  • Brain imaging
  • Histamine H receptor
  • Positron emission tomography (PET)
  • Radiosynthesis

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry

Cite this

A new facile synthetic route to [11C]GSK189254, a selective PET radioligand for imaging of CNS histamine H3 receptor. / Wang, Min; Gao, Mingzhang; Steele, Brandon L.; Glick-Wilson, Barbara E.; Brown-Proctor, Clive; Shekhar, Anantha; Hutchins, Gary; Zheng, Qi-Huang.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 22, No. 14, 15.07.2012, p. 4713-4718.

Research output: Contribution to journalArticle

Wang, Min ; Gao, Mingzhang ; Steele, Brandon L. ; Glick-Wilson, Barbara E. ; Brown-Proctor, Clive ; Shekhar, Anantha ; Hutchins, Gary ; Zheng, Qi-Huang. / A new facile synthetic route to [11C]GSK189254, a selective PET radioligand for imaging of CNS histamine H3 receptor. In: Bioorganic and Medicinal Chemistry Letters. 2012 ; Vol. 22, No. 14. pp. 4713-4718.
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