Synthesis of a radioiodinated analogue of the serotonin 5-HT(2A) receptor ligand RP 62203

John R. Lever, Suzanne M. Johnson

Research output: Contribution to journalArticlepeer-review

Abstract

An analogue of RP 62203 having radioiodine in the 4-position of the 1,8-naphthosultam ring system has been prepared for evaluation as a ligand for the serotonin 5-HT(2A) receptor. Non-radioactive 4-iodo-RP 62203 was synthesized in three steps (20% overall yield) by iodination of 1,8-naphthosultam with iodine monochloride followed by N-alkylation with 1-bromo-3-chloropropane and coupling with 1-(4-fluorophenyl)piperazine. The precursor for radiolabeling was prepared in 83% yield from 4-iodo-RP 62203 and hexamethylditin by palladium-mediated trimethylstannylation. Electrophilic radioiododestannylation gave 4-[125I]-Rp 62203 in good isolated yield (80-86%), with high purity (≤ 99.6%) and specific radioactivity (1200-2066 mCi/CLmol).

Original languageEnglish (US)
Pages (from-to)143-150
Number of pages8
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume41
Issue number2
DOIs
StatePublished - Feb 1 1998

Keywords

  • RP 62203
  • Radioiodine
  • Serotonin receptor

ASJC Scopus subject areas

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

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