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Other names for **2-[4-(Methylamino)phenyl]benzothiazol-6-ol** include **6-OH-BTA-1** and **Pittsburgh Compound B (PiB)**. 2-[4-(Methylamino)phenyl]benzothiazol-6-ol is a β-amyloid imaging agent used in positron emission tomography (PET) for detecting amyloid plaques in vivo. It can be efficiently radiolabeled with carbon-11 ([11C]) using reactive methylating agents like [11C]methyl triflate or [11C]methyl nona-fluorobutyl-1-sulfonate ([11C]MeONf), yielding high radiochemical purity without requiring protection of the 6-hydroxy group. The synthesis can be performed via solution-phase or solid-phase methods, with the latter offering advantages such as reduced precursor usage, elimination of HPLC purification, and faster production times, making it suitable for clinical applications.

566170-04-5

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566170-04-5 Usage

Type of compound

Synthetic chemical compound

Applications

Dye in the textile industry
Biological stain in medical and biological research
Treatment for medical conditions such as methemoglobinemia, malaria, cyanide poisoning
Potential treatment for neurodegenerative conditions like Alzheimer's and Parkinson's disease
Potential anti-cancer properties and use in photodynamic therapy for cancer treatment

Check Digit Verification of cas no

The CAS Registry Mumber 566170-04-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 5,6,6,1,7 and 0 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 566170-04:
(8*5)+(7*6)+(6*6)+(5*1)+(4*7)+(3*0)+(2*0)+(1*4)=155
155 % 10 = 5
So 566170-04-5 is a valid CAS Registry Number.

566170-04-5Downstream Products

566170-04-5Relevant articles and documents

A rapid one-step radiosynthesis of the β-amyloid imaging radiotracer N-methyl-[11C]2-(4′-methylaminophenyl)-6-hydroxybenzothiazole ([11C]-6-OH-BTA-1)

Wilson, Alan A.,Garcia, Armando,Chestakova, Alexandra,Kung, Hank,Houle, Sylvain

, p. 679 - 682 (2004)

The promising β-amyloid PET imaging agent, [11C]-6-OH-BTA- 1, has been radiolabelled in one step using [11C]-methyl triflate. No protection of the 6-hydroxy group is required, greatly simplifying the synthetic method. The reaction may be carried out in solution or by the captive solvent 'loop' method. Copyright

Highly efficient solid phase supported radiosynthesis of [11C]PiB using tC18 cartridge as a “3-in-1” production entity

Boudjemeline, Mehdi,Hopewell, Robert,Rochon, Pierre-Luc,Jolly, Dean,Hammami, Iness,Villeneuve, Sylvia,Kostikov, Alexey

, p. 632 - 638 (2017)

Pittsburgh compound B ([11C]PiB) is the gold standard positron emission tomography (PET) tracer for the in vivo imaging of amyloid plaques. Currently, it is synthesized by either solution chemistry or using a “dry loop” approach followed by HPLC purification within 30?minutes starting from [11C]CO2. Here, we report a novel, highly efficient solid phase supported carbon-11 radiolabeling procedure using commercially available disposable tC18 cartridge as a “3-in-1” entity: reactor, purifier, and solvent replacement system. [11C]PiB is synthesized by passing gaseous [11C]CH3OTf through a tC18 cartridge preloaded with a solution of precursor. Successive elution with aqueous ethanol solutions allows for nearly quantitative separation of the reaction mixture to provide chemically and radiochemically pure PET tracer. [11C]PiB suitable for human injection is produced within 10?minutes starting from [11C]CH3OTf (20?min from [11C]CO2) in 22% isolated yield not corrected for decay and molar activity of 190?GBq/μmol using 0.2?mg of precursor. This technique reduces the amount of precursor and other supplies, avoids use of preparative HPLC and toxic solvents, and decreases the time between consecutive production batches. Solid phase supported technique can facilitate [11C]PiB production compliant with Good Manufacturing Practice (GMP) and improve synthesis reliability.

Preparation of [11C]methyl nona-fluorobutyl-1-sulfonate ([ 11C]MeONf) and its use in the synthesis of [11C]-6-OH-BTA- 1

Jolly, Dean,Lakhrissi, Younes,Kovacevic, Miriam M.,Chertkow, Howard,Schirrmacher, Ralf

, p. 1230 - 1233 (2007)

The rapid, simple and high-yield synthesis of the extraordinarily reactive 11C-methylating agent, [11C]methyl nona-fluorobutyl-1- sulfonate ([11C]MeONf), and its use in the synthesis of the promising β-amyloid imaging agent, [11C]-6-OH-BTA-1, is reported. In terms of radioactive methylation yields, [11C]MeONf seems to surpass [11C]methyl trifluoromethansulfonate ([11C]MeOTf) as a methylating agent in this particular case giving the 11C-labelled compound in high-preparative radiochemical yields between 27 and 29% EOS with a minimum formation of radioactive by-products. Copyright

Highlighting the versatility of the Tracerlab synthesis modules. Part 2: Fully automated production of [11C]-labeled radiopharmaceuticals using a Tracerlab FXC-Pro

Shao, Xia,Hoareau, Raphael,Runkle, Adam C.,Tluczek, Louis J. M.,Hockley, Brian G.,Henderson, Bradford D.,Scott, Peter J. H.

experimental part, p. 819 - 838 (2012/03/27)

The field of radiochemistry is moving toward exclusive use of automated synthesis modules for production of clinical radiopharmaceutical doses. Such a move not only comes with many advantages but also presents radiochemists with the challenge of re-configuring synthesis modules for production of radiopharmaceuticals that require non-conventional radiochemistry while maintaining full automation. Herein, we continue our series of articles showcasing the versatility of the Tracerlab FX synthesis modules by presenting straightforward, fully automated methods for preparing a range of carbon-11 labeled radiopharmaceuticals using a Tracerlab FXC-Pro. Strategies for production of [11C]acetate, [11C]carfentanil, [ 11C]choline, [11C]3-amino-4-[2-[(di(methyl)amino)methyl] phenyl]sulfanylbenzonitrile ([11C]DASB), (+)-a-[11C] dihydroterabenazine ([11C]DTBZ), [11C]flumazenil ([ 11C]FMZ), meta-hydroxyephedrine ([11C]HED), [ 11C]methionine, [11C]PBR28, [11C]Pittsburgh Compound B ([11C]PiB), 1-[11C]methylpiperidin-4-yl propionate ([11C]PMP), and [11C]raclopride are presented.

Synthesis and evaluation of 11C-labeled 6-substituted 2-arylbenzothiazoles as amyloid imaging agents.

Mathis, Chester A,Wang, Yanming,Holt, Daniel P,Huang, Guo-Feng,Debnath, Manik L,Klunk, William E

, p. 2740 - 2754 (2007/10/03)

The synthesis and evaluation of a series of neutral analogues of thioflavin-T (termed BTA's) with high affinities for aggregated amyloid and a wide range of lipophilicities are reported. Radiolabeling with high specific activity [(11)C]methyl iodide provided derivatives for in vivo evaluation. Brain entry in control mice and baboons was high for nearly all of the analogues at early times after injection, but the clearance rate of radioactivity from brain tissue varied by more than 1 order of magnitude. Upon the basis of its rapid clearance from normal mouse and baboon brain tissues, [N-methyl-(11)C]2-(4'-methylaminophenyl)-6-hydroxybenzothiazole (or [(11)C]6-OH-BTA-1) was selected as the lead compound for further evaluation. The radiolabeled metabolites of [(11)C]6-OH-BTA-1 were polar and did not enter brain. The binding affinities of [N-methyl-(3)H]6-OH-BTA-1 for homogenates of postmortem AD frontal cortex and synthetic Abeta(1-40) fibrils were similar (K(d) = 1.4 nM and 4.7 nM, respectively), but the ligand-to-Abeta peptide binding stoichiometry was approximately 400-fold higher for AD brain than Abeta(1-40) fibrils. Staining of AD frontal cortex tissue sections with 6-OH-BTA-1 indicated the selective binding of the compound to amyloid plaques and cerebrovascular amyloid. The encouraging in vitro and in vivo properties of [(11)C]6-OH-BTA-1 support the choice of this derivative for further evaluation in human subject studies of brain Abeta deposition.

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