407582-16-5

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 7460-82-4 diethylene glycol ditosylate 

Downstream Products

• 1118608-65-3 (6-[(S)-(4-chlorophenyl)(1H-1,2,4-triazol-1-yl)methyl]-1-[2-(2-[¹⁸F]fluoroethoxy)ethyl]-1H-benzotriazole) 
• 1355047-41-4 C₇H₇O₃S^(1-)*C₂₂H₂₃⁽¹⁸⁾FOP⁽¹⁺⁾ 
• 1416006-58-0 C₃₂H₃₈⁽¹⁸⁾FN₂O₄⁽¹⁺⁾*C₇H₇O₃S^(1-) 

Relevant academic research and scientific papers

Design, Synthesis, and Evaluation of Thienodiazepine Derivatives as Positron Emission Tomography Imaging Probes for Bromodomain and Extra-Terminal Domain Family Proteins

To better understand the role of bromodomain and extra-terminal domain (BET) proteins in epigenetic mechanisms, we developed a series of thienodiazepine-based derivatives and identified two compounds, 3a and 6a, as potent BET inhibitors. Further in vivo pharmacokinetic studies and analysis of in vitro metabolic stability of 6a revealed excellent brain penetration and reasonable metabolic stability. Compounds 3a and 6a were radiolabeled with fluorine-18 in two steps and utilized in positron emission tomography (PET) imaging studies in mice. Preliminary PET imaging results demonstrated that [18F]3a and [18F]6a have good brain uptake (with maximum SUV = 1.7 and 2, respectively) and binding specificity in mice brains. These results show that [18F]6a is a potential PET radiotracer that could be applied to imaging BET proteins in the brain. Further optimization and improvement of the metabolic stability of [18F]6a are still needed in order to create optimal PET imaging probes of BET family members.

Novel [18F]-Labeled Meta-Bromobenzylguanidine Derivatives: Potential Positron Emission Tomography Imaging Probes for the Norepinephrine Transporter

To develop novel norepinephrine transporter (NET)-targeting positron emission tomography (PET) probes with optimal pharmacokinetic properties, a series of meta-bromobenzylguanidine derivatives was synthesized. 4-Fluorodiethoxyethane-3-bromobenzylguanidine (compound 12) showed relatively good affinity for the NET (IC50 = 1.00 ± 0.04 μM). The corresponding radiotracer 18F-12 was prepared in high radiochemical purity (>98%) via a three-step method. The in vitro cellular uptake results demonstrated that 18F-12 was specifically taken up by NET-expressing SK-N-SH cells by the uptake-1 mechanism. Biodistribution studies in mice showed that 18F-12 exhibited high cardiac uptake (10.45 ± 0.66 %ID/g at 5 min p.i. and 6.44 ± 0.40 %ID/g at 120 min p.i.), faster liver clearance, and a lower dose of absorbed radiation than [123I]-labeled meta-iodobenzylguanidine ([123I]MIBG). Small animal PET imaging confirmed the high heart-to-background ratio of 18F-12 and the uptake-1 mechanism specific for the NET in rats, indicating its potential as a promising PET radiotracer for cardiac sympathetic nerve imaging.

Development of Novel 18F-PET Agents for Tumor Hypoxia Imaging

Tumor hypoxia is a major factor responsible for tumor progression, metastasis, invasion, and treatment resistance, leading to low local tumor control and recurrence after radiotherapy in cancers. Here,18F-positron emission tomography (PET) probes are developed for visualizing viable hypoxic cells in biopsies. Pimonidazole derivatives and nitroimidazole-based agents bearing sulfonyl linkers were evaluated. A small-animal PET study showed that the tumor uptake of [18F]-23 [poly(ethylene glycols) (PEG)-sulfonyl linker] of 3.36 ± 0.29%ID/g was significantly higher (P 0.01) than that of [18F]-20 (piperazine-linker tracer, 2.55 ± 0.49%ID/g) at 2 h postinjection in UPPL tumors. The tumor-to-muscle uptake ratio of [18F]-23 (2.46 ± 0.48 at 2 h pi) was well improved compared with that of [18F]-FMISO (1.25 ± 0.14 at 2 h pi). A comparable distribution pattern was observed between ex vivo autoradiography of [18F]-23 and pimonidazole staining of the neighboring slice, indicating that [18F]-23 is a promising PET agent for hypoxia imaging.

Positron probe, and preparation method and application thereof

The invention discloses a positron probe, and a preparation method and an application thereof. The positron probe is a F-labeled positron probe, and has a structural formula shown in the description. The positron probe has the advantages of simplicity and rapidness in preparation, high yield and high specific activity, can be used for broad-spectrum PET imaging of tumors, and has clinical values of diagnosing and monitoring treatment effects. The preparation method of the probe is simple and rapid, can realize fully-automatic production, and can meet scientific research and clinical requirements.

A PET contrast compound for early diagnosis of cardiovascular diseases and use thereof

The present invention provides: a precursor compound for the production of a radioactive compound for efficient imaging of heart; a radioactive compound produced using the precursor compound; and uses thereof as a contrast medium for PET imaging. According to the present invention, it is an object of the present invention to provide an improved novel PET imaging compound having a low water absorption rate and an improved removal rate in the liver.COPYRIGHT KIPO 2019

Fluorine-18 labeled rhodamine derivatives for imaging with positron emission tomography

The present invention is directed toward novel fluorine-18 labeled rhodamine dye derivatives and methods of making the same. The present invention is also directed toward methods of using novel fluorine-18 labeled rhodamine dye derivatives as positron emi

Synthesis of [18F]-labeled (2-(2-fluoroethoxy)ethyl) triphenylphosphonium cation as a potential agent for myocardial imaging using positron emission tomography

[18F]-labeled molecular probe for the detection of myocardial perfusion deficit is driving particular interest due to its high clinical applicability. Thus, we synthesized (2-(2-[18F]fluoroethoxy)ethyl) triphenylphosphonium salt ([s

Effect of the prosthetic group on the pharmacologic properties of 18F-labeled rhodamine b, a potential myocardial perfusion agent for positron emission tomography (PET)

We recently reported the development of the 2-[18F]fluoroethyl ester of rhodamine B as a potential positron emission tomography (PET) tracer for myocardial perfusion imaging. This compound, which was prepared using a [18F]fluoroethyl prosthetic group, has significant uptake in the myocardium in rats but also demonstrates relatively high liver uptake and is rapidly hydrolyzed in vivo in mice. We have now prepared 18F-labeled rhodamine B using three additional prosthetic groups (propyl, diethylene glycol, and triethylene glycol) and found that the prosthetic group has a significant effect on the in vitro and in vivo properties of these compounds. Of the esters prepared to date, the diethylene glycol ester is superior in terms of in vitro stability and pharmacokinetics. These observations suggest that the prosthetic group plays a significant role in determining the pharmacological properties of 18F-labeled compounds. They also support the value of continued investigation of 18F-labeled rhodamines as PET radiopharmaceuticals for myocardial perfusion imaging.

18F-Labelled vorozole analogues as PET tracer for aromatase

One- and two-step syntheses for the 18F-labelling of 6-[(S)-(4-chlorophenyl)(1H-1,2,4-triazol-1-yl)methyl]-1-(2-[18F] fluoroethyl)-1H-benzotriazole, [18F]FVOZ, 1 and 6-[(S)-(4- chlorophenyl)(1H-1,2,4-triazol-1-yl)methyl]-1-[2-(2-[18F] fluoroethoxy)ethyl]-1H-benzotriazole, [18F]FVOO, 2 were developed. In the two-step synthesis, the nucleophilic fluorination step was performed by reacting (S)-6-[(4-chlorophenyl)-(1H-1,2,4-triazol-1-yl)methyl]-1H-benzotriazole (VOZ) with either the 18F-labelled ethane-1,2-diyl bis(4-methylbenzenesulfonate) or the oxydiethane-2,1-diyl bis(4- methylbenzenesulfonate). The radiochemical yields were in the range of 9-13% after the 110-120 min total syntheses and the specific radioactivities were 175 ± 7 GBq/μmol and 56 GBq/μmol for compounds 1 and 2, respectively. In the one-step synthesis, the precursor 2-{6-[(4-chlorophenyl)(1H-1,2,4- triazol-1-yl)methyl]-1H-1,2,3-benzotriazol-1-yl}ethyl 4-methylbenzenesulfonate (7) or 1-[2-(2-bromoethoxy)ethyl]-6-[(4-chlorophenyl)(1H-1,2,4-triazol-1-yl) methyl]-1H-benzotriazole (8) was directly labelled via an 18F nucleophilic substitution to give the corresponding tracer. The labelled compounds were obtained in 36-99% radiochemical yield after 75-min syntheses. The specific radioactivities are 100 GBq/μmol for compound 1 and 80 GBq/μmol for compound 2. In vitro autoradiography using frozen rat brains illustrated specific binding in the medial amygdala, the bed nucleus of stria terminalis and the preoptic area, all of which corresponded well to the result of 11C-labelled vorozole. Copyright