Synthesis and amine transporter affinities of novel phenyltropane derivatives as potential positron emission tomography (PET) imaging agents

A series of novel fluoroalkyl-containing tropane derivatives (6-8, 10-14, 17, and 18) were synthesized from cocaine. Novel compounds were evaluated for affinity and selectivity in competitive radioligand binding assays selective for cerebral serotonin (5-HT), dopamine (DA), and norepinephrine (NE) t...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2004-11, Vol.14 (22), p.5635-5639
Main Authors: XUEMEI PENG, AO ZHANG, KULA, Nora S, BALDESSARINI, Ross J, NEUMEYER, John L
Format: Article
Language:English
Subjects:
Animals
Binding, Competitive
Biogenic Amines - metabolism
Biological and medical sciences
Brain - drug effects
Brain - metabolism
Carrier Proteins - antagonists & inhibitors
Carrier Proteins - metabolism
Contrast media. Radiopharmaceuticals
Medical sciences
Miscellaneous
Molecular Structure
Pharmacology. Drug treatments
Positron-Emission Tomography - methods
Radioligand Assay
Rats
Structure-Activity Relationship
Tropanes - chemical synthesis
Tropanes - chemistry
Tropanes - pharmacology
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Summary:A series of novel fluoroalkyl-containing tropane derivatives (6-8, 10-14, 17, and 18) were synthesized from cocaine. Novel compounds were evaluated for affinity and selectivity in competitive radioligand binding assays selective for cerebral serotonin (5-HT), dopamine (DA), and norepinephrine (NE) transporters (SERT, DAT, and NET). The nortropane-fluoroalkyl esters (7, 10, 11) were most potent for SERT (K(i): 0.18, 0.24, and 0.30 nM, respectively). Tosylate esters 17 and 18, synthesized as precursors for [(18)F]-labeled, Positron Emission Tomography (PET) imaging agents, also showed high affinity for DAT.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2004.08.049