Category: 92-36-4

Klunk, William E. published the artcileUncharged thioflavin-T derivatives bind to amyloid-beta protein with high affinity and readily enter the brain, Application of 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Life Sciences (2001), 69(13), 1471-1484, database is CAplus and MEDLINE.

In vivo assessment of the beta-sheet proteins deposited in amyloid plaques (Aβ peptide) or neurofibrillary tangles (tau protein) presents a target for the development of biol. markers for Alzheimer’s disease (AD). In an effort to develop in vivo beta-sheet imaging probes, derivatives of thioflavin-T (ThT) were synthesized and evaluated. These compounds lack the pos. charged quaternary heterocyclic nitrogen of ThT and are therefore uncharged at physiol. pH. They are 600-fold more lipophilic than ThT. These ThT derivatives bind to Aβ(1-40) fibrils with higher affinity (K_i = 20.2 nM) than ThT (K_i = 890 nM). The uncharged ThT derivatives stained both plaques and neurofibrillary tangles in post-mortem AD brain, showing some preference for plaque staining. A carbon-11 labeled compound, [N-methyl-¹¹C]6-Me-BTA-1, was prepared, and its brain entry and clearance were studied in Swiss-Webster mice. This compound entered the brain at levels comparable to commonly used neuroreceptor imaging agents (0.223% ID-kg/g or 7.61% ID/g at 2 min post-injection) and showed good clearance of free and non-specifically bound radioactivity in normal rodent brain tissue (brain clearance t_1/2 = 20 min). The combination of relatively high affinity for amyloid, specificity for staining plaques and neurofibrillary tangles in post-mortem AD brain, and good brain entry and clearance makes [N-methyl-¹¹C]6-Me-BTA-1 a promising candidate as an in vivo positron emission tomog. (PET) beta-sheet imaging agent.

Life Sciences published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C14H12N2S, Application of 2-(4-Aminophenyl)-6-methylbenzothiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Rutkauskaite, Andzelika published the artcileSupramolecular self-associating amphiphiles: determination of molecular self-association properties and calculation of critical micelle concentration using a high-throughput, optical density based methodology, SDS of cas: 92-36-4, the publication is Organic & Biomolecular Chemistry (2022), 20(30), 5999-6006, database is CAplus and MEDLINE.

Supramol. self-associating amphiphiles are a class of amphiphilic salt, the anionic component of which is ′frustratedâ€?in nature, meaning multiple hydrogen bonding modes can be accessed simultaneously. Here we derive critical micelle concentration values for four supramol. self-associating amphiphiles using the standard pendant drop approach and present a new high-throughput, optical d. measurement based methodol., to enable the estimation of critical micelle concentrations over multiple temperatures In addition, we characterize the low-level hydrogen bonded self-association events in the solid state, through single crystal X-ray diffraction, and in polar organic DMSO-d₆ solutions using a combination of ¹H NMR techniques. Moving into aqueous ethanol solutions (EtOH/H₂O or EtOH/D₂O (1 : 19 volume/volume)), we also show these amphiphilic compounds to form higher-order self-associated species through a combination of ¹H NMR, dynamic light scattering and zeta potential studies.

Organic & Biomolecular Chemistry published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C14H12N2S, SDS of cas: 92-36-4.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Lei, Yingjie published the artcileSynthesis of 2-(4-aminophenyl)benzothiazoles using MF resin supported H⁺ under solvent free conditions, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Russian Journal of General Chemistry (2015), 85(3), 679-682, database is CAplus.

A simple and convenient approach to 2-(4-aminophenyl)benzothiazole derivatives by condensation of o-aminothiophenol with (un)substituted p-aminobenzoic acid under the action of melamine formaldehyde resin (MFR) supported sulfuric acid under microwave irradiation (MW) and solvent-free conditions has been developed. Structures of the corresponding products were elucidated by IR, ¹H NMR spectra, and elemental anal. The resin could be easily recovered and reused for subsequent reactions.

Russian Journal of General Chemistry published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C14H12N2S, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Millard, B. J. published the artcileHigh resolution mass spectrometry. II. Substituted benzothiazoles, Name: 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Organic Mass Spectrometry (1968), 1(2), 285-94, database is CAplus.

The mass spectra of 19 substituted benzothiazoles have been recorded and the identity of the various ions in the mass spectra has been established by high resolution (accurate) mass measurement. Deuterium labeling has been used to elucidate the fragmentation processes of these compounds The parent compound of the series, benzothiazole, exhibits the loss of HCN and CS from the parent ion as the most important decomposition pathways. The H atom concerned in the loss of HCN originates from the 2-position of benzothiazole, while in 2-substituted benzothiazoles, different mechanisms are apparent for the loss of HCN, and these are clarified by D labeling. Some substituted benzothiazoles can lose S from their mol. ions, a process which does not occur in benzothiazole itself. The substituted benzothiazoles undergo many other types of fragmentations, in some cases retaining the substituent, and in other cases losing it prior to collapse of the thiazole ring.

Organic Mass Spectrometry published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C14H12N2S, Name: 2-(4-Aminophenyl)-6-methylbenzothiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Ukrainets, I. V. published the artcile4-Hydroxy-2-quinolones 148. Synthesis and antitubercular activity of 1-hydroxy-3-oxo-6,7-dihydro-3H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid N-R-amides, Application of 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Chemistry of Heterocyclic Compounds (New York, NY, United States) (2008), 44(8), 956-966, database is CAplus.

A method for the synthesis of the title compound [i.e., 1-hydroxy-3-oxo-6,7-dihydro-3H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid N-amides] is reported here. A reaction of 1,2,3,4-tetrahydroquinoline with methanetricarboxylic acid 1,1,1-tri-Et ester provided an ester compound [i.e., 2,3-dihydro-7-hydroxy-5-oxo-1H,5H-benzo[ij]quinolizine-6-carboxylic acid Et ester]. The above-mentioned amides were prepared from this intermediate by a reaction with primary amines. A comparative anal. has been carried out of the antitubercular activity of the compounds thus prepared with active structural analogs.

Chemistry of Heterocyclic Compounds (New York, NY, United States) published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C26H26N4O7, Application of 2-(4-Aminophenyl)-6-methylbenzothiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Sagnou, Marina published the artcileA Phenylbenzothiazole Conjugate with the Tricarbonyl fac-[M(I)(CO)₃]⁺ (M = Re, ⁹⁹Tc, ^99mTc) Core for Imaging of β-Amyloid Plaques, Computed Properties of 92-36-4, the publication is European Journal of Inorganic Chemistry (2012), 2012(27), 4279-4286, S4279/1-S4279/6, database is CAplus.

The 2-(4′-aminophenyl)-6-methylbenzothiazole that is known to display affinity and specificity toward the amyloid plaques of Alzheimer’s disease (AD) has been joined to the tricarbonyl [M(CO)₃NNO] chelate (M = Re, ⁹⁹Tc, and ^99mTc) through a five-carbon linker chain to generate the neutral complex (1) (namely, Re-1 for M = Re; 99Tc-1 for M = ⁹⁹Tc; and 99mTc-1 for M = ^99mTc) with the aim of developing a single-photon emission computed tomog. (SPECT) radiodiagnostic agent for AD. Re-1 was characterized by spectroscopic methods and x-ray crystallog., whereas the detailed NMR spectroscopic anal. of 99Tc-1 demonstrated its structural similarity to Re-1. Complexes Re-1 and 99Tc-1 display selective binding affinity for amyloid plaques as evidenced by fluorescence spectroscopy, whereas the biodistribution data of 99mTc-1 characterized by relatively low brain uptake, fast clearance from brain and blood, and in vivo stability are considered encouraging for further elaboration on the structural features of 1 in the direction of increased brain uptake.

European Journal of Inorganic Chemistry published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C14H12N2S, Computed Properties of 92-36-4.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Solbach, C. published the artcileEfficient radiosynthesis of carbon-11 labelled uncharged Thioflavin T derivatives using [¹¹C]methyl triflate for β-amyloid imaging in Alzheimer’s Disease with PET, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Applied Radiation and Isotopes (2005), 62(4), 591-595, database is CAplus and MEDLINE.

The synthesis of carbon-11 amino function labeled uncharged Thioflavin T derivatives is known to be performed by reaction of the demethyl-precursors with [¹¹C]methyl iodide but the labeling yields are only mediocre. The use of [¹¹C]methyl triflate improved the radiochem. yield of three potential β-amyloid imaging PET-radiotracers significantly. Performance of the labeling reaction by reacting the corresponding precursor mols. with [¹¹C]methyl triflate for 1 min at 80° led to radiochem. yields of 44±10% (n = 5) for [¹¹C]6-Me-BTA-1, 68±4% (n = 10) for [¹¹C]BTA-1 and 58±2% (n = 5) for [¹¹C]6-OH-BTA-1 with respect to [¹¹C]methyl triflate. In production runs (60 min, 50 μA) up to 6500 MBq (mean: 4000±1900 MBq) of [¹¹C]6-Me-BTA-1, 7900 MBq (mean: 6000±1000 MBq) of [¹¹C]BTA-1 and 7100 MBq (mean: 6300±600 MBq) of [¹¹C]6-OH-BTA-1 could be obtained ready for i.v. injection. The radiochem. purity was >95% with specific activities in the range of 80-120 GBq/μmol (EOS) within a total synthesis time of less than 40 min after EOB.

Applied Radiation and Isotopes published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C12H15NO, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Du, Hongying published the artcileClassification structure-activity relationship (CSAR) studies for prediction of genotoxicity of thiophene derivatives, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Toxicology Letters (2008), 177(1), 10-19, database is CAplus and MEDLINE.

The grid search support vector machine (GS-SVM) was used to build a classification structure-activity relationship (CSAR) model and to predict the genotoxicity property of 140 thiophene derivatives with the information derived from the compounds’ mol. structures. The seven descriptors selected by linear discriminant anal. (LDA) were used as the inputs to develop the GS-SVM model. Using the Grid Search method, a satisfactory model with a good predictive capability was obtained. The quality of the models was evaluated by the number of right classified compounds The total accuracy of the LDA model was 81.4% and 85.2% for the training set and test set, resp., and to the GS-SVM model was 92.9% and 92.6%, resp. It was proved that the GS-SVM method was a very useful modeling approach with good classification ability for the genotoxicity of the thiophene derivatives This work also provides a new idea and an alternative method to investigate the genotoxicity of the similar structures with thiophene derivatives, and can be extended to other toxicity studies.

Toxicology Letters published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C14H12N2S, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Kuhnert-Brandstaetter, Maria published the artcileThermal analytical and infrared spectroscopic investigations on polymorphic organic compounds. V., Computed Properties of 92-36-4, the publication is Mikrochimica Acta (1989), 3(1-2), 125-36, database is CAplus.

All the polymorphic compounds described are enantiotropic, so that in four cases, order-disorder or rotational transformation can be deduced on the basis of the relationships between enthalpy of transformation and enthalpy of fusion. The following compounds are of this type: (±)-1-azabicyclo[2.2.2]octan-3-ol (4 modifications), 5-norbornene-2,3-dicarboxylic anhydride (3 modifications), (1R)-(-)-camphorquinone (3 modifications) and 2-bromoethylamine-HBr (3 modifications). For tris(acetylacetonato)aluminum(III) (3 modifications) and 2-(4-aminophenyl)-6-methylbenzothiazole (5 modifications), another type of transformation must be assumed.

Mikrochimica Acta published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C14H12N2S, Computed Properties of 92-36-4.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Lee, Nathanael J. published the artcileHexa (ethylene glycol) derivative of benzothiazole aniline promotes dendritic spine formation through the RasGRF1-Ras dependent pathway, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Biochimica et Biophysica Acta, Molecular Basis of Disease (2016), 1862(2), 284-295, database is CAplus and MEDLINE.

The authors’ recent study demonstrated that an amyloid-β binding mol., BTA-EG4, increases dendritic spine number via Ras-mediated signaling. To potentially optimize the potency of the BTA compounds, the authors synthesized and evaluated an amyloid-β binding analog of BTA-EG4 with increased solubility in aqueous solution, BTA-EG6. The authors initially examined the effects of BTA-EG6 on dendritic spine formation and found that BTA-EG6-treated primary hippocampal neurons had significantly increased dendritic spine number compared to control treatment. In addition, BTA-EG6 significantly increased the surface level of AMPA receptors. Upon investigation into the mol. mechanism by which BTA-EG6 promotes dendritic spine formation, the authors found that BTA-EG6 may exert its effects on spinogenesis via RasGRF1-ERK signaling, with potential involvement of other spinogenesis-related proteins such as Cdc42 and CDK5. Taken together, the authors’ data suggest that BTA-EG6 boosts spine and synapse number, which may have a beneficial effect of enhancing neuronal and synaptic function in the normal healthy brain.

Biochimica et Biophysica Acta, Molecular Basis of Disease published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C14H12N2S, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica