Synthesis of a novel 123I‐labelled derivative of GBR12783, a potential agent for SPECT imaging of dopamine‐reuptake sites

Xiao‐Shu ‐S He, Kan Sam Lee, Daniel Weinberger, Brian R. de Costa

Research output: Contribution to journalArticlepeer-review

Abstract

[123I]1‐[2‐(Diphenylmethoxy)ethyl]‐4‐[3‐(m‐iodophenyl)‐2‐propenyl]piperazine ([123I]2), a potential SPECT imaging agent for dopamine reuptake sites was efficiently synthesized in 4 steps from 1‐[2‐(diphenylmethoxy)ethyl]piperazine (3). A key step in the synthesis was the selective AIH3‐mediated reduction of 1[2‐(diphenylmethoxy)ethyl‐4‐(m‐bromocinnamoyl] piperazine (4) to 1‐[2‐(diphenylmethoxy)ethyl‐4‐(3‐(m‐bromophenyl)‐2‐propenyl]piperazine(5). The 123I label of [123I]2 was introduced in the final step in up to 90% radiochemical yield by treatment of the organotin precursor 1‐(2‐(diphenylmethoxy)ethyl‐4‐[3‐[(m‐(tributyl stannyl)phenyl]‐2‐propenyl]piperazine (6) with Na123I in aqueous CH3CO3H.

Original languageEnglish (US)
Pages (from-to)493-500
Number of pages8
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume33
Issue number6
DOIs
StatePublished - Jun 1993
Externally publishedYes

Keywords

  • 1‐[2‐(diphenylmethoxy)ethyl]‐4‐[3‐[(m‐(tributyl stannyl)phenyl]‐2‐propenyl]piperazine (6)
  • SPECT
  • [I]1‐[2‐(Diphenylmethoxy)ethyl]‐4‐[3‐(m‐iodophenyl)‐2‐propenyl]piperazine ([I]2)
  • dopamine reuptake
  • organotin

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Radiology Nuclear Medicine and imaging
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis of a novel <sup>123</sup>I‐labelled derivative of GBR12783, a potential agent for SPECT imaging of dopamine‐reuptake sites'. Together they form a unique fingerprint.

Cite this