115109-21-2Relevant articles and documents
A general protocol for Cu-mediated fluoro-deamination: Sandmeyer fluorination of diverse aromatic substrates
Pérez-García, R. Manuel,Gr?nnevik, Gaute,Riss, Patrick J.
, p. 1011 - 1015 (2021)
A Cu(I)-mediated fluoro-deamination method for nucleophilic radiofluorination was devised. The method affords fluorinated aromatic products directly from anilines under both no-carrier added and stoichiometric conditions. Isolated radiochemical yields ran
A microwave radiosynthesis of the 4-[18F]-fluorobenzyltriphenylphosphonium ion
Ravert, Hayden T.,Holt, Daniel P.,Dannals, Robert F.
, p. 695 - 698 (2014)
The 4-[18F]-fluorobenzyltriphenylphosphonium cation was synthesized by a series of microwave reactions from no carrier added [18F]-fluoride. The microwave procedure reduced the quantity of reagents used and synthesis time when compared with the original synthesis. In addition, problematic solid phase extraction, sodium borohydride reduction by column and inconsistent yields with excessive precipitate formation during the bromination step were eliminated. The 4-[18F]-fluorobenzyltriphenylphosphonium cation was produced radiochemically pure in 8.3% yield with a specific radioactivity of 534.5 ± 371.4 GBq/μmole at end of synthesis.
Rapid synthesis of maleimide functionalized fluorine-18 labeled prosthetic group using “radio-fluorination on the Sep-Pak” method
Basuli, Falguni,Zhang, Xiang,Jagoda, Elaine M.,Choyke, Peter L.,Swenson, Rolf E.
, p. 599 - 605 (2018)
Following our recently published fluorine-18 labeling method, “Radio-fluorination on the Sep-Pak”, we have successfully synthesized 6-[18F]fluoronicotinaldehyde by passing a solution (1:4 acetonitrile: t-butanol) of its quaternary ammonium salt
FASTlab Radiosynthesis of the 18F-labelled HER2-binding Affibody molecule [18F]GE-226
Glaser, Matthias,Grigg, Julian,Hiscock, Duncan,Indrevoll, Bard,Iveson, Peter B.,Luthra, Sajinder K.,Mantzilas, Dimitrios,Omtvedt, Lone,Shales, Jonathan
, p. 925 - 932 (2019)
An 18F-labelled human epidermal growth factor receptor (HER2) receptor binding radiotracer is a potential tool to non-invasively identify HER2 positive tumour lesions in subjects with recurrent metastatic breast cancer. Having explored the manu
Minimalist approach meets green chemistry: Synthesis of 18F- labeled (hetero)aromatics in pure ethanol
Zlatopolskiy, Boris D.,Zischler, Johannes,Krapf, Philipp,Richarz, Raphael,Lauchner, Katharina,Neumaier, Bernd
, p. 404 - 410 (2019)
The application of toxic solvents and additives is inevitable for most of the described protocols for 18F-labeling. Herein, a novel “green” procedure for nucleophilic aromatic radiofluorination of highly activated (hetero)aromatic substrates in
Concerted nucleophilic aromatic substitution with 19F- and 18F-
Neumann, Constanze N.,Hooker, Jacob M.,Ritter, Tobias
, p. 369 - 373 (2016)
Nucleophilic aromatic substitution (S N Ar) is widely used by organic chemists to functionalize aromatic molecules, and it is the most commonly used method to generate arenes that contain 18 F for use in positron-emission tomography (PET) imaging. A wide range of nucleophiles exhibit S N Ar reactivity, and the operational simplicity of the reaction means that the transformation can be conducted reliably and on large scales. During S N Ar, attack of a nucleophile at a carbon atom bearing a a €leaving group' leads to a negatively charged intermediate called a Meisenheimer complex. Only arenes with electron-withdrawing substituents can sufficiently stabilize the resulting build-up of negative charge during Meisenheimer complex formation, limiting the scope of S N Ar reactions: The most common S N Ar substrates contain strong I €-Acceptors in the ortho and/or para position(s). Here we present an unusual concerted nucleophilic aromatic substitution reaction (CS N Ar) that is not limited to electron-poor arenes, because it does not proceed via a Meisenheimer intermediate. We show a phenol deoxyfluorination reaction for which CS N Ar is favoured over a stepwise displacement. Mechanistic insights enabled us to develop a functional-group-Tolerant 18 F-deoxyfluorination reaction of phenols, which can be used to synthesize 18 F-PET probes. Selective 18 F introduction, without the need for the common, but cumbersome, azeotropic drying of 18 F, can now be accomplished from phenols as starting materials, and provides access to 18 F-labelled compounds not accessible through conventional chemistry.
Radiosynthesis and preliminary biological evaluation of a new 18F-labeled triethylene glycol derivative of triphenylphosphonium
Tominaga, Takahiro,Ito, Hiroaki,Ishikawa, Yoichi,Iwata, Ren,Ishiwata, Kiichi,Furumoto, Shozo
, p. 117 - 123 (2016)
Delocalized lipophilic cations such as [18F]fluorobenzyltriphenylphosphonium ([18F]FBnTP) can accumulate in mitochondria and have been used in myocardial perfusion imaging (MPI). In this study, we established a simplified method for
Synthesis of Carbon-11-, Fluorine-18-, and Iodine-125-Labeled GABAA-Gated Chloride Ion Channel Blockers: Substituted 5-tert-Butyl-2-phenyl-1,3-dithianes and -dithiane Oxides
Snyder, Scott E.,Kume, Akito,Jung, Yong-Woon,Connor, Stephen E.,Sherman, Philip S.,et al.
, p. 2663 - 2671 (1995)
A series of substituted 5-tert-butyl-2-phenyl-1,3-dithianes and 5-tert-butyl-2-phenyl-1,1,3,3-tetraoxo-1,3-dithianes was synthesized as ligands for the GABAA receptor complex-associated neuronal chloride ion channels.The in vitro binding affini
1-(4-[18F]Fluorobenzyl)-4-[(tetrahydrofuran-2-yl)methyl]piperazine: A Novel Suitable Radioligand with Low Lipophilicity for Imaging σ1 Receptors in the Brain
He, Yingfang,Xie, Fang,Ye, Jiajun,Deuther-Conrad, Winnie,Cui, Bixiao,Wang, Liang,Lu, Jie,Steinbach, J?rg,Brust, Peter,Huang, Yiyun,Lu, Jie,Jia, Hongmei
, p. 4161 - 4172 (2017)
We have designed and synthesized novel piperazine compounds with low lipophilicity as σ1 receptor ligands. 1-(4-Fluorobenzyl)-4-[(tetrahydrofuran-2-yl)methyl]piperazine (10) possessed a low nanomolar σ1 receptor affinity and a high selectivity toward the vesicular acetylcholine transporter (>2000-fold), σ2 receptors (52-fold), and adenosine A2A, adrenergic α2, cannabinoid CB1, dopamine D1, D2L, γ-aminobutyric acid A (GABAA), NMDA, melatonin MT1, MT2, and serotonin 5-HT1 receptors. The corresponding radiotracer [18F]10 demonstrated high brain uptake and extremely high brain-to-blood ratios in biodistribution studies in mice. Pretreatment with the selective σ1 receptor agonist SA4503 significantly reduced the level of accumulation of the radiotracer in the brain. No radiometabolite of [18F]10 was observed to enter the brain. Positron emission tomography and magnetic resonance imaging confirmed suitable kinetics and a high specific binding of [18F]10 to σ1 receptors in rat brain. Ex vivo autoradiography showed a reduced level of binding of [18F]10 in the cortex and hippocampus of the senescence-accelerated prone (SAMP8) compared to that of the senescence-accelerated resistant (SAMR1) mice, indicating the potential dysfunction of σ1 receptors in Alzheimer’s disease.
Access to 18F-labelled isoxazoles by ruthenium-promoted 1,3-dipolar cycloaddition of 4-[18F]fluoro-N-hydroxybenzimidoyl chloride with alkynes
Roscales, Silvia,Kniess, Torsten
, p. 393 - 403 (2019)
4-[18F]Fluoro-N-hydroxybenzimidoyl chloride (18FBIC), an 18F-labelled aromatic nitrile oxide, was developed as building block for Ru-promoted 1,3-dipolar cycloaddition with alkynes. 18FBIC is obtained in a one-p
