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

doi:10.1002/jlcr.647

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 journal › Article › peer-review

21 Scopus citations

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 language	English (US)
Pages (from-to)	93-98
Number of pages	6
Journal	Journal of Labelled Compounds and Radiopharmaceuticals
Volume	46
Issue number	1
DOIs	https://doi.org/10.1002/jlcr.647
State	Published - Jan 2003
Externally published	Yes

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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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. / Katoch-Rouse, Reeti; Horti, Andrew G.
In: Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 46, No. 1, 01.2003, p. 93-98.

Research output: Contribution to journal › Article › peer-review

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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%.",

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