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JOURNAL ARTICLE
RESEARCH SUPPORT, NON-U.S. GOV'T
Synthesis of carbon-11-labeled 5-HT 6 R antagonists as new candidate PET radioligands for imaging of Alzheimer's disease.
Bioorganic & Medicinal Chemistry Letters 2018 June 2
Carbon-11-labeled serotonin (5-hydroxytryptamine) 6 receptor (5-HT6 R) antagonists, 1-[(2-bromophenyl)sulfonyl]-5-[11 C]methoxy-3-[(4-methyl-1-piperazinyl)methyl]-1H-indole (O-[11 C]2a) and 1-[(2-bromophenyl)sulfonyl]-5-methoxy-3-[(4-[11 C]methyl-1-piperazinyl)methyl]-1H-indole (N-[11 C]2a), 5-[11 C]methoxy-3-((4-methylpiperazin-1-yl)methyl)-1-(phenylsulfonyl)-1H-indole (O-[11 C]2b) and 5-methoxy-3-((4-[11 C]methylpiperazin-1-yl)methyl)-1-(phenylsulfonyl)-1H-indole (N-[11 C]2b), 1-((4-isopropylphenyl)sulfonyl)-5-[11 C]methoxy-3-((4-methylpiperazin-1-yl)methyl)-1H-indole (O-[11 C]2c) and 1-((4-isopropylphenyl)sulfonyl)-5-methoxy-3-((4-[11 C]methylpiperazin-1-yl)methyl)-1H-indole (N-[11 C]2c), 1-((4-fluorophenyl)sulfonyl)-5-[11 C]methoxy-3-((4-methylpiperazin-1-yl)methyl)-1H-indole (O-[11 C]2d) and 1-((4-fluorophenyl)sulfonyl)-5-methoxy-3-((4-[11 C]methylpiperazin-1-yl)methyl)-1H-indole (N-[11 C]2d), were prepared from their O- or N-desmethylated precursors with [11 C]CH3 OTf through O- or N-[11 C]methylation and isolated by HPLC combined with SPE in 40-50% radiochemical yield, based on [11 C]CO2 and decay corrected to end of bombardment (EOB). The radiochemical purity was >99%, and the molar activity (MA) at EOB was 370-740 GBq/μmol with a total synthesis time of ∼40-min from EOB.
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