Radiosynthesis of 5-(2-(4-pyridinyl)vinyl)-6-chloro-3-(1-[(11)C]methyl-2-(S)-pyrrolidinylmethoxy)pyridine, a high affinity ligand for studying nicotinic acetylcholine receptors by positron emission tomography

L L Brown; O Pavlova; A Mukhin; A S Kimes; A G Horti

doi:10.1016/s0968-0896(01)00224-3

Radiosynthesis of 5-(2-(4-pyridinyl)vinyl)-6-chloro-3-(1-[(11)C]methyl-2-(S)-pyrrolidinylmethoxy)pyridine, a high affinity ligand for studying nicotinic acetylcholine receptors by positron emission tomography

Bioorg Med Chem. 2001 Nov;9(11):3055-8. doi: 10.1016/s0968-0896(01)00224-3.

Authors

L L Brown¹, O Pavlova, A Mukhin, A S Kimes, A G Horti

Affiliation

¹ Brain Imaging Center, National Institute on Drug Abuse, National Institutes of Health, 5500 Nathan Shock Drive, Baltimore, MD 21224, USA. laverneb@prodigy.net

PMID: 11597489
DOI: 10.1016/s0968-0896(01)00224-3

Abstract

5-(2-(4-pyridinyl)vinyl)-6-chloro-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine (1b) exhibited high affinity for nicotinic acetylcholine receptors in the in vitro competition binding assays, with a K(d) value in the low picomolar range, performed at room temperature and at physiological temperature. An efficient radiochemical synthesis of 5-(2-(4-pyridinyl)vinyl)-6-chloro-3-(1-[(11)C]methyl-2-(S)-pyrrolidinylmethoxy)pyridine (1c), a potential tracer for the study of nAChR by positron emission tomography, has been developed.

MeSH terms

Animals
Binding, Competitive
Brain / cytology
Carbon Radioisotopes
Cell Membrane / chemistry
Ligands
Pyridines / chemical synthesis*
Pyridines / metabolism
Pyrrolidines / chemical synthesis*
Pyrrolidines / metabolism
Radioligand Assay
Radiopharmaceuticals / chemical synthesis*
Radiopharmaceuticals / metabolism
Rats
Receptors, Nicotinic / analysis*
Receptors, Nicotinic / metabolism
Tomography, Emission-Computed*

Substances

5-(2-(4-pyridinyl)vinyl)-6-chloro-3-(1-methyl-2-pyrrolidinylmethoxy)pyridine
Carbon Radioisotopes
Ligands
Pyridines
Pyrrolidines
Radiopharmaceuticals
Receptors, Nicotinic