Synthesis of [123I]-8-[4-[2-(5-iodothienyl)]-4-oxobutyl]-3-methyl-1- phenyl-1,3,8-triazaspiro[4.5]decan-4-one

A potential dopamine D2 receptor radioligand for SPECT

Rikki N. Waterhouse, J. Timothy Gotsick, George Kabalka, Mark M. Goodman, J. C. O'Brien

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

[123I]-8-[4-[2-(5-Iodothienyl)]-4-oxobutyl]-3-methyl-1-phenyl-1,3,8- triazaspiro[4.5]-decan-4-one (1) has been synthesized as a potential ligand for dopamine D2 receptors. This new compound proved to be moderate in lipophilicity (log P = 3.14) and exhibited high affinity (Ki = 1.9 nM) for the dopamine D2 receptor as well as good selectivity for D2 versus serotonin 5HT2 receptors (Ki 5HT2/D2 = 16.7) in vitro. The corresponding radioligand, 123I-1, was synthesized from a thienyl tributylstannane precursor using oxidative iododestannylation methods. The radiochemical yield was 64-80% EOS (n = 5) and the purified product was >99% radiochemically purity with a specific activity >3,500 mCi/μmol (>129,500 MBq/μmol).

Original languageEnglish (US)
Pages (from-to)363-376
Number of pages14
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume41
Issue number5
DOIs
StatePublished - May 1 1998
Externally publishedYes

Fingerprint

Dopamine D2 Receptors
Single-Photon Emission-Computed Tomography
Serotonin Receptors
Ligands
8-(4-(2-(5-iodothienyl))-4-oxobutyl)-3-methyl-1-phenyl-1,3,8-triazaspiro(4.5)decan-4-one
In Vitro Techniques
tributyltin

All Science Journal Classification (ASJC) codes

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

Cite this

Synthesis of [123I]-8-[4-[2-(5-iodothienyl)]-4-oxobutyl]-3-methyl-1- phenyl-1,3,8-triazaspiro[4.5]decan-4-one : A potential dopamine D2 receptor radioligand for SPECT. / Waterhouse, Rikki N.; Gotsick, J. Timothy; Kabalka, George; Goodman, Mark M.; O'Brien, J. C.

In: Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 41, No. 5, 01.05.1998, p. 363-376.

Research output: Contribution to journalArticle

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abstract = "[123I]-8-[4-[2-(5-Iodothienyl)]-4-oxobutyl]-3-methyl-1-phenyl-1,3,8- triazaspiro[4.5]-decan-4-one (1) has been synthesized as a potential ligand for dopamine D2 receptors. This new compound proved to be moderate in lipophilicity (log P = 3.14) and exhibited high affinity (Ki = 1.9 nM) for the dopamine D2 receptor as well as good selectivity for D2 versus serotonin 5HT2 receptors (Ki 5HT2/D2 = 16.7) in vitro. The corresponding radioligand, 123I-1, was synthesized from a thienyl tributylstannane precursor using oxidative iododestannylation methods. The radiochemical yield was 64-80{\%} EOS (n = 5) and the purified product was >99{\%} radiochemically purity with a specific activity >3,500 mCi/μmol (>129,500 MBq/μmol).",
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