High molar activity of [11C]TCH346 via [11C]methyl triflate using the “wet” [11C]CO2 reduction method

Neumaier, Bernd; Stüsgen, Stefan; Lang, Markus; Roden, W.; Coenen, Heinz H.

doi:10.1016/j.apradiso.2007.08.001

Cited by 6 publications

(3 citation statements)

References 18 publications

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“…The product was eluted from the cartridge with 4 mL of diethylether, then the solvent evaporated in vacuo (800 up to 330 mbar) and the product re-dissolved in 100–300 µL of ethanol. The molar activity was determined by HPLC using a UV mass calibration curve as described earlier in detail [58].…”

Section: Methodsmentioning

confidence: 99%

4-[18F]Fluorophenylpiperazines by Improved Hartwig-Buchwald N-Arylation of 4-[18F]fluoroiodobenzene, Formed via Hypervalent λ3-Iodane Precursors: Application to Build-Up of the Dopamine D4 Ligand [18F]FAUC 316

et al. 2014

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Substituted phenylpiperazines are often neuropharmacologically active compounds and in many cases are essential pharmacophores of neuroligands for different receptors such as D2-like dopaminergic, serotoninergic and other receptors. Nucleophilic, no-carrier-added (n.c.a.) Different palladium catalysts and solvents were tested with particular attention to the polar solvents dimethylformamide (DMF) and dimethylsulfoxide (DMSO). Weak inorganic bases like potassium phosphate or cesium carbonate seem to be essential for the arylation step and lead to conversation rates above 70% in DMF which is comparable to those in typically used toluene. In DMSO even quantitative conversation was observed. Overall radiochemical yields of up to 40% and 60% in DMF and DMSO, respectively, were reached depending on the labelling yield of the first step. The fluorophenylpiperazine obtained was coupled in a third reaction step with 2-formyl-1H-indole-5-carbonitrile to yield the highly selective dopamine D4 ligand [

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Section: Methodsmentioning

confidence: 99%

4-[18F]Fluorophenylpiperazines by Improved Hartwig-Buchwald N-Arylation of 4-[18F]fluoroiodobenzene, Formed via Hypervalent λ3-Iodane Precursors: Application to Build-Up of the Dopamine D4 Ligand [18F]FAUC 316

et al. 2014

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“…Therefore, benzyl-and benzodioxinpiperazine moieties were separately synthesized as intermediates and coupled afterwards. Analogous to the description of Liu et al, 22 the latter intermediate 1-(1,4-benzodioxin-6-yl)piperazine (2) was synthesized via cyclization of the commercially available aminodioxin 2,3-dihydrobenzo[b]- [1,4]dioxin-6-amine with bis(2-chloroethyl)amine hydrochloride in diethylene glycol or diethylene glycol monomethyl ether 15 (cf. Scheme 2).…”

Section: Chemistrymentioning

confidence: 99%

“…Determination of molar activities was carried out according to standard procedures by means of the previously described semi-preparative HPLC, comparing UV-signals under radioactivity peaks with a calibration UV/mass-curve, as described earlier. 15 Radio TLC chromatograms were analyzed by UV detection and on a Packard Instant Imager. 1 H, 13 C, and 19 F NMR spectra were recorded on a Bruker DPX Avance 200 spectrometer with samples dissolved in CDCl 3 or DMSO-d 6 .…”

Section: Experimental Generalmentioning

confidence: 99%

Labeling of benzodioxin piperazines with fluorine‐18 as prospective radioligands for selective imaging of dopamine D₄ receptors

Kügler

Neumaier

Coenen

2013

Labelled Comp Radiopharmac

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The D(4) receptor is of high interest for research and clinical application but puts high demands on appropriate radioligands to be useful tools for investigation. Search for adequate radioligands suitable for in vivo imaging is therefore still in progress. The potential neuroleptic drug 6-(4-[4-fluorobenzyl]piperazin-1-yl)benzodioxin shows high affinity and selectivity to the D(4) receptor. Derivatization of this lead structure by adding hydrophilic moieties was carried out in order to lower its lipophilicity what led to three new putative dopamine receptor D(4) ligands. A comprehensive description of the syntheses of standard compounds and corresponding labeling precursors is given which were obtained in satisfactory yields. Furthermore, the radiosyntheses by direct (18) F-labeling and build-up synthesis were compared. All derivatives of 6-(4-[4-fluorobenzyl]-piperazin-1-yl)benzodioxin were successfully synthesized in (18) F-labeled form with radiochemical yields of 9-35% and molar activities of 30-60 GBq/µmol using one-pot procedures.

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Radiochemistry with Carbon‐11

Thompson

Kealey

Sephton

et al. 2020

Handbook of Radiopharmaceuticals

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High molar activity of [11C]TCH346 via [11C]methyl triflate using the “wet” [11C]CO2 reduction method

Cited by 6 publications

References 18 publications

4-[18F]Fluorophenylpiperazines by Improved Hartwig-Buchwald N-Arylation of 4-[18F]fluoroiodobenzene, Formed via Hypervalent λ3-Iodane Precursors: Application to Build-Up of the Dopamine D4 Ligand [18F]FAUC 316

4-[18F]Fluorophenylpiperazines by Improved Hartwig-Buchwald N-Arylation of 4-[18F]fluoroiodobenzene, Formed via Hypervalent λ3-Iodane Precursors: Application to Build-Up of the Dopamine D4 Ligand [18F]FAUC 316

Labeling of benzodioxin piperazines with fluorine‐18 as prospective radioligands for selective imaging of dopamine D₄ receptors

Radiochemistry with Carbon‐11

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High molar activity of [11C]TCH346 via [11C]methyl triflate using the “wet” [11C]CO2 reduction method

Cited by 6 publications

References 18 publications

4-[18F]Fluorophenylpiperazines by Improved Hartwig-Buchwald N-Arylation of 4-[18F]fluoroiodobenzene, Formed via Hypervalent λ3-Iodane Precursors: Application to Build-Up of the Dopamine D4 Ligand [18F]FAUC 316

4-[18F]Fluorophenylpiperazines by Improved Hartwig-Buchwald N-Arylation of 4-[18F]fluoroiodobenzene, Formed via Hypervalent λ3-Iodane Precursors: Application to Build-Up of the Dopamine D4 Ligand [18F]FAUC 316

Labeling of benzodioxin piperazines with fluorine‐18 as prospective radioligands for selective imaging of dopamine D4 receptors

Radiochemistry with Carbon‐11

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Labeling of benzodioxin piperazines with fluorine‐18 as prospective radioligands for selective imaging of dopamine D₄ receptors