Synthesis of 6-chloro-3-((2-(S)-azetidinyl)methoxy)-5-(2-[ 18F]fluoropyridin-4-yl)pyridine ([18F]NIDA 522131), a novel potential radioligand for studying extrathalamic nicotinic acetylcholine receptors by PET

Yi Zhang; Andrew G. Horti

doi:10.1002/jlcr.883

Synthesis of 6-chloro-3-((2-(S)-azetidinyl)methoxy)-5-(2-[ ¹⁸F]fluoropyridin-4-yl)pyridine ([¹⁸F]NIDA 522131), a novel potential radioligand for studying extrathalamic nicotinic acetylcholine receptors by PET

Yi Zhang, Andrew G. Horti

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

12 Scopus citations

Abstract

6-Chloro-3-((2-(S)-azetidinyl)methoxy)-5-(2-[¹⁸F]fluoropyridin- 4-yl)pyridine ([¹⁸F]NIDA 522131), a potential radioligand for studying extrathalamic nicotinic acetylcholine receptors by positron-emission tomography, was synthesized via no-carrier-added nucleophilic [ ¹⁸F]fluorination of 6-chloro-3-((1-(tert-butoxycarbonyl)-2-(S)- azetidinyl) methoxy)-5-(2-iodopyridin-4-yl)vinyl)pyridine, followed by acidic deprotection. The overall radiochemical yield of the radiosynthesis was 4-8% (non-decay-corrected), the specific radioactivity was in the range of 167-33 GBq/μmol (4500-9000 mCi/μmol) and the radiochemical purity was greater than 99%. Preparation of [¹⁸F]NIDA522131 via corresponding bromo-derivative 2 is also described.

Original language	English (US)
Pages (from-to)	947-952
Number of pages	6
Journal	Journal of Labelled Compounds and Radiopharmaceuticals
Volume	47
Issue number	13
DOIs	https://doi.org/10.1002/jlcr.883
State	Published - Nov 2004
Externally published	Yes

Keywords

F
Nicotinic acetylcholine receptors
Nucleophilic halogen-exchange
Positron emission tomography

ASJC Scopus subject areas

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

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Synthesis of 6-chloro-3-((2-(S)-azetidinyl)methoxy)-5-(2-[ ¹⁸F]fluoropyridin-4-yl)pyridine ([¹⁸F]NIDA 522131), a novel potential radioligand for studying extrathalamic nicotinic acetylcholine receptors by PET. / Zhang, Yi; Horti, Andrew G.
In: Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 47, No. 13, 11.2004, p. 947-952.

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

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title = "Synthesis of 6-chloro-3-((2-(S)-azetidinyl)methoxy)-5-(2-[ 18F]fluoropyridin-4-yl)pyridine ([18F]NIDA 522131), a novel potential radioligand for studying extrathalamic nicotinic acetylcholine receptors by PET",

abstract = "6-Chloro-3-((2-(S)-azetidinyl)methoxy)-5-(2-[18F]fluoropyridin- 4-yl)pyridine ([18F]NIDA 522131), a potential radioligand for studying extrathalamic nicotinic acetylcholine receptors by positron-emission tomography, was synthesized via no-carrier-added nucleophilic [ 18F]fluorination of 6-chloro-3-((1-(tert-butoxycarbonyl)-2-(S)- azetidinyl) methoxy)-5-(2-iodopyridin-4-yl)vinyl)pyridine, followed by acidic deprotection. The overall radiochemical yield of the radiosynthesis was 4-8% (non-decay-corrected), the specific radioactivity was in the range of 167-33 GBq/μmol (4500-9000 mCi/μmol) and the radiochemical purity was greater than 99%. Preparation of [18F]NIDA522131 via corresponding bromo-derivative 2 is also described.",

keywords = "F, Nicotinic acetylcholine receptors, Nucleophilic halogen-exchange, Positron emission tomography",

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