ArticleBioorganic & medicinal chemistry2012
Synthesis and evaluation of in vitro bioactivity for vesicular acetylcholine transporter inhibitors containing two carbonyl groups.
Article in Bioorganic & medicinal chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- The Benzoylpiperidine Fragment as a Privileged Structure in Medicinal Chemistry: A Comprehensive Review.Molecules (Basel, Switzerland) · 2024Review
- In vitro characterization of [European journal of pharmacology · 2021Article
- Radiosynthesis and evaluation of a fluorine-18 labeled radioligand targeting vesicular acetylcholine transporter.Bioorganic & medicinal chemistry letters · 2018Article
- Exploration of Sulfur-Containing Analogues for Imaging Vesicular Acetylcholine Transporter in the Brain.ChemMedChem · 2018Article
- Kinetic modeling of [Journal of neurochemistry · 2018Article
- Synthesis, resolution, and in vitro evaluation of three vesicular acetylcholine transporter ligands and evaluation of the lead fluorine-18 radioligand in a nonhuman primate.Organic & biomolecular chemistry · 2017Article
- Kinetics modeling and occupancy studies of a novel C-11 PET tracer for VAChT in nonhuman primates.Nuclear medicine and biology · 2016Article
- Further validation to support clinical translation of [(18)F]FTC-146 for imaging sigma-1 receptors.EJNMMI research · 2015Article
- Synthesis and biological characterization of a promising F-18 PET tracer for vesicular acetylcholine transporter.Bioorganic & medicinal chemistry · 2015Article
- In vitro and ex vivo characterization of (-)-TZ659 as a ligand for imaging the vesicular acetylcholine transporter.European journal of pharmacology · 2015Article
- In vitro and in vivo characterization of two C-11-labeled pet tracers for vesicular acetylcholine transporter.Molecular imaging and biology · 2014Article
- Striatal dopamine D1-like receptor binding is unchanged in primary focal dystonia.Movement disorders : official journal of the Movement Disorder Society · 2013Article
- Heteroaromatic and aniline derivatives of piperidines as potent ligands for vesicular acetylcholine transporter.Journal of medicinal chemistry · 2013Article
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Authors and funding
7 authors.
Funding
Abstract
To identify selective high-affinity ligands for the vesicular acetylcholine transporter (VAChT), we have incorporated a carbonyl group into the structures of trozamicol and prezamicol scaffolds, and also converted the secondary amines of the piperidines of trozamicols and prezamicols into amides. Of 18 new racemic compounds, 4 compounds displayed high affinity for VAChT (K(i)=10-20 nM) and greater than 300-fold selectivity for VAChT over σ(1) and σ(2) receptors, namely (4-(4-fluorobenzoyl)-4'-hydroxy-[1,3'-bipiperidin]-1'-yl)(3-methylthiophen-2-yl)methanone oxalate (9g) (K(i-VAChT)=11.4 nM, VAChT/σ(1)=1063, VAChT/σ(2)=370), (1'-benzoyl-4'-hydroxy-[1,3'-bipiperidin]-4-yl)(4-methoxyphenyl)methanone oxalate (10c) (K(i-VAChT)=15.4 nM, VAChT/σ(1)=374, VAChT/σ(2)=315), (4'-hydroxy-1'-(thiophene-2-carbonyl)-[1,3'-bipiperidin]-4-yl)(4-methoxyphenyl)methanone oxalate (10e) (K(i-VAChT)=19.0 nM, VAChT/σ(1)=1787, VAChT/σ(2)=335), and (4'-hydroxy-1'-(3-methylthiophene-2-carbonyl)-[1,3'-bipiperidin]-4-yl)(4-methoxyphenyl)methanone oxalate (10g) (K(i-VAChT)=10.2 nM, VAChT/σ(1)=1500, VAChT/σ(2)=2030). These four compounds can be radiosynthesized with C-11 or F-18 to validate their possibilities of serving as PET probes for quantifying the levels of VAChT in vivo.
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