Synthesis of carbon-11-labeled aminoalkylindole derivatives as new candidates of cannabinoid receptor radioligands for PET imaging of alcohol abuse

Carbon-11-labeled aminoalkylindole derivatives (1-butyl-7-[(11)C]methoxy-1H-indol-3-yl)(naphthalene-1-yl)methanone ([(11)C]3), 1-butyl-7-[(11)C]methoxy-3-(naphthalene-1-ylmethyl)-1H-indole ([(11)C]5), and 1-butyl-7-[(11)C]methoxy-3-(naphthalene-2-yl)-1H-indole ([(11)C]8) were prepared by O-[(11)C]me...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2014-12, Vol.24 (24), p.5581-5586
Main Authors: Gao, Mingzhang, Gao, Andy Chufan, Wang, Min, Zheng, Qi-Huang
Format: Article
Language:English
Subjects:
Alcoholism - diagnosis
Alcoholism - diagnostic imaging
Carbon Radioisotopes - chemistry
Humans
Indoles - chemical synthesis
Indoles - chemistry
Isotope Labeling
Ligands
Positron-Emission Tomography
Radiography
Radiopharmaceuticals - chemical synthesis
Radiopharmaceuticals - chemistry
Receptors, Cannabinoid - chemistry
Receptors, Cannabinoid - metabolism
Solid Phase Extraction
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Summary:Carbon-11-labeled aminoalkylindole derivatives (1-butyl-7-[(11)C]methoxy-1H-indol-3-yl)(naphthalene-1-yl)methanone ([(11)C]3), 1-butyl-7-[(11)C]methoxy-3-(naphthalene-1-ylmethyl)-1H-indole ([(11)C]5), and 1-butyl-7-[(11)C]methoxy-3-(naphthalene-2-yl)-1H-indole ([(11)C]8) were prepared by O-[(11)C]methylation of their corresponding precursors with [(11)C]CH3OTf under basic condition (2N NaOH) and isolated by a simplified solid-phase extraction (SPE) method in 50-60% radiochemical yields based on [(11)C]CO2 and decay corrected to end of bombardment (EOB). The overall synthesis time from EOB was 23 min, the radiochemical purity was >99%, and the specific activity at end of synthesis (EOS) was 185-555 GBq/μmol.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2014.10.097