Synthesis of N-(piperidin-1-yl)-5-(4-methoxyphenyl)-1-(2-chlorophenyl)-4- [18F]fluoro-1H-pyrazole-3-carboxamide by nucleophilic [18F] fluorination: A PET radiotracer for studying CB1 cannabinoid receptors

Reeti Katoch-Rouse, Andrew G. Horti

Research output: Contribution to journalArticle

Abstract

The feasibility of nucleophilic displacement of bromide in the 4-bromopyrazole ring with [18F]fluoride has been demonstrated by the synthesis of two radiolabeled compounds: N-(piperidin-1-yl)-5-(4-methoxyphenyl)-1- (2-chlorophenyl)-4-[18F]fluoro-1H -pyrazole-3-carboxamide, ([18F] NIDA-42033) 1b and 1-(2-chlorophenyl)-4-[18F]fluoro-5-(4-methoxyphenyl)- 1H-pyrazole-3-carboxylic acid, ethyl ester 4. The radiochemical yields were in the range of 1-6%. [18]NIDA-42033, a potential radiotracer for the study of CB1 cannabinoid receptors in the animal brain by positron emission tomography, has been synthesized in sufficient quantities with specific radioactivity greater than 2500 mCi/μmol and radiochemical purity >95%.

Original languageEnglish (US)
Pages (from-to)93-98
Number of pages6
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume46
Issue number1
DOIs
StatePublished - Jan 1 2003
Externally publishedYes

Keywords

  • Cannabinoid receptors
  • F
  • Nucleophilic radiofluorination
  • Positron emission tomography
  • Radiosynthesis

ASJC Scopus subject areas

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

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