Category: 92-36-4

Ma, Dawei published the artcileEfficient and economical access to substituted benzothiazoles: copper-catalyzed coupling of 2-haloanilides with metal sulfides and subsequent condensation, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Angewandte Chemie, International Edition (2009), 48(23), 4222-4225, S4222/1-S4222/18, database is CAplus and MEDLINE.

The first metal-catalyzed direct coupling of metal sulfides with aryl halides and subsequent intramol. condensation provided substituted benzothiazoles. A wide range of functional groups are tolerated under the reaction conditions.

Angewandte Chemie, International Edition 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

Cai, Mingzhong published the artcileRecyclable copper-catalyzed cyclization of o-haloanilides and metal sulfides: An efficient and practical access to substituted benzothiazoles, Name: 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Molecular Catalysis (2022), 112115, database is CAplus.

An efficient heterogeneous copper-catalyzed cyclization of o-haloanilides and metal sulfides has been achieved via the C-S coupling in DMF at 80 or 140° in the existence of an MCM-41-bound NHC-Cu(I) catalyst and then intramol. condensation, delivering a wide range of substituted benzothiazoles in mostly good to high yields. This new MCM-41-NHC-CuI complex can facilely be obtained by a two-step procedure starting from easily accessible and inexpensive reagents and reused more than seven times without any significant loss of its catalytic efficiency. The present protocol has been successfully applied to the gram-scale synthesis of two antitumor agents 5F203 and PMX 610.

Molecular Catalysis 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

Zheng, Ming-Qiang published the artcileSynthesis of 2-(4-aminophenyl)benzothiazole derivatives and determination of their activity as PET tracers for human brain β-amyloid peptides, Computed Properties of 92-36-4, the publication is Youji Huaxue (2007), 27(11), 1369-1373, database is CAplus.

A series of novel 2-(4-aminophenyl)-6-substituted benzothiazole derivatives were prepared and evaluated as potential β-amyloid PET (positron emission tomog.) tracers. Were prepared from proper 2-amino-6-substituted benzothiazole derivatives through basic hydrolysis, intermol. cycloaddition and N/O-alkylation reactions. Their structures were confirmed by IR, ¹H NMR, EI/ESI-MS, HRMS spectra and elemental anal. The sequence of binding affinity of some compounds with human brain homogenate was analyzed.

Youji Huaxue 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 C7H4ClIO2, Computed Properties of 92-36-4.

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

Ambure, Pravin published the artcileExploring Structural Requirements of Imaging Agents Against Aβ Plaques in Alzheimer’s Disease: A QSAR Approach, Application of 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Combinatorial Chemistry & High Throughput Screening (2015), 18(4), 411-419, database is CAplus and MEDLINE.

Exploring mol. imaging agents against the beta amyloid (Aβ) plaques for an early detection of Alzheimer’s disease (AD) is one of the emerging research areas in medicinal chem. In the present <i>in-silico</i> study, a congeneric series of 44 imaging agents, including 17 positron emission tomog. (PET) and 27 single photon emission computed tomog. (SPECT) imaging agents, was utilized to understand the structural features required for having essential binding affinity against Aβ plaques. Here, 2D-quant. structure-activity relationship (2D-QSAR) and group-based QSAR (G-QSAR) models have been developed using genetic function approximation (GFA) and validated using various statistical metrics. Both the models showed satisfactory performance signifying the reliability and robustness of the developed QSAR models. The vital information gained from both the QSAR models will be useful in developing new PET and SPECT imaging agents and also in predicting their binding affinity against Aβ plaques. The results of this study would be important in view of the widespread clin. applicability of the SPECT imaging agents, especially in the developing countries. In this study, we have also designed some imaging agents based on the information provided by the models. Some of these designed compounds were predicted to be similar to or more active than the most active imaging agents present in the original dataset.

Combinatorial Chemistry & High Throughput Screening 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

Tzanopoulou, Stamatia published the artcileEvaluation of Re and 99mTc Complexes of 2-(4′-Aminophenyl)benzothiazole as Potential Breast Cancer Radiopharmaceuticals, Safety of 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Journal of Medicinal Chemistry (2010), 53(12), 4633-4641, database is CAplus and MEDLINE.

The synthesis of M(I)(CO)₃(NNO) (M = Re, ^99mTc) complexes conjugated to the antitumor agent 2-(4′-aminophenyl)benzothiazole and to its 6-Me derivative, as well as their in vitro and in vivo biol. evaluation as breast cancer radiopharmaceuticals, is reported. The Re complexes displayed under the fluorescence microscope clear uptake by the sensitive to the 2-(4′-aminophenyl)benzothiazole pharmacophore breast cancer cell lines MCF-7 and T47D, while uptake by less sensitive lines and by normal fibroblasts was much weaker. In accordance, uptake of the corresponding radioactive ^99mTc complexes was clearly higher in the breast cancer cell lines MCF-7 and MDA-231 compared to normal fibroblasts. Biodistribution of the ^99mTc complexes in SCID mice bearing MCF-7 xenografts showed appreciable tumor uptake. A tumor/muscle ratio of 2.2 was measured for the complex conjugated to 2-(4′-aminophenyl)benzothiazole that led to successful tumor imaging. The results render the 2-(4′-aminophenyl)benzothiazole complexes potential candidates for imaging (^99mTc) and targeted radiotherapy (¹⁸⁸Re) of breast cancer.

Journal of Medicinal 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 C16H12O, Safety of 2-(4-Aminophenyl)-6-methylbenzothiazole.

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

Ichihara, Osamu published the artcileDevelopment of self-indicating resin, Computed Properties of 92-36-4, the publication is Combinatorial Chemistry & High Throughput Screening (2007), 10(4), 261-267, database is CAplus and MEDLINE.

The development and application of self-indicating resins (SIR), materials which can indicate the presence or absence of amines in the reaction solution by the conspicuous color change of a phenolsulfophthalein type dye immobilized on resin beads has been reported. Although the functionality necessary for attaching the dye to the resins could be readily introduced by the Suzuki-Miyaura coupling during the synthesis of the SIR, this approach was only applicable to the dyes containing suitable functionality for the cross-coupling reaction. A new approach to immobilizing the indicating dyes onto the resin support is now reported. The dyes suitable for loading onto aminomethyl polystyrene (PS) resin were prepared by Friedel-Crafts reaction of 2-sulfoterephthalic anhydride with a wide range of phenols. Using this new route, polymer-supported dye I was readily prepared in >100g quantities. Use of I in the synthesis of a 144 member urea library was demonstrated and the SIR successfully indicated the endpoint of the reaction between amines and isocyanates.

Combinatorial Chemistry & High Throughput Screening 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

Prangkio, Panchika published the artcileSelf-assembled, cation-selective ion channels from an oligo(ethylene glycol) derivative of benzothiazole aniline, Name: 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Biochimica et Biophysica Acta, Biomembranes (2011), 1808(12), 2877-2885, database is CAplus and MEDLINE.

This paper describes the spontaneous formation of well-defined pores in planar lipid bilayers from the self-assembly of a small synthetic mol. that contains a benzothiazole aniline (BTA) group attached to a tetra-ethylene glycol (EG₄) moiety. Macroscopic and single-channel current recordings suggest that these pores are formed by the assembly of four BTA-EG₄ monomers with an open pore diameter that appears similar to the one of gramicidin pores (∼0.4 nm). The single-channel conductance of these pores is modulated by the pH of the electrolyte and has a min. at pH ∼3. Self-assembled pores from BTA-EG₄ are selective for monovalent cations and have long open channel lifetimes on the order of seconds. BTA-EG₄ monomers in these pores appear to be arranged sym. across both leaflets of the bilayer, and spectroscopy studies suggest that the fluorescent BTA group is localized inside the lipid bilayers. In terms of biol. activity, BTA-EG₄ mols. inhibited growth of gram-pos. Bacillus subtilis bacteria (IC₅₀ ∼50 μM) and human neuroblastoma SH-SY5Y cells (IC₅₀ ∼60 μM), while they were not toxic to gram-neg. Escherichia coli bacteria at a concentration up to 500 μM. Based on these properties, this drug-like, synthetic, pore-forming mol. with a mol. weight below 500 g mol^-1 might be appealing as a starting material for development of antibiotics or membrane-permeating moieties for drug delivery. From a biophys. point of view, long-lived, well-defined ion-selective pores from BTA-EG₄ mols. offer an example of a self-assembled synthetic supramol. with biol. function.

Biochimica et Biophysica Acta, Biomembranes 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

Ali-Torres, Jorge published the artcileInsights on the Binding of Thioflavin Derivative Markers to Amyloid-Like Fibril Models from Quantum Chemical Calculations, Application In Synthesis of 92-36-4, the publication is Journal of Physical Chemistry B (2013), 117(22), 6674-6680, database is CAplus and MEDLINE.

Thioflavin-T (ThT) is one of the most widely used dyes for staining and identifying amyloid fibrils, which share a common parallel in register β-sheet structure. Unfortunately, ThT is a charged mol., which limits its ability to cross the blood brain barrier and its use as an efficient dye for in vivo detection of amyloid fibrils. For this reason, several uncharged ThT derivatives have been designed and their binding properties to Aβ fibrils studied by fluorescence assays. However, there are still many unknowns on the binding mechanism and the role of noncovalent interactions on the affinity of these ligands toward β-sheet structures. The present contribution analyzes the binding of ThT (1) and neutral ThT derivatives (2-7) to a β-sheet model by means of quantum chem. B3LYP-D calculations and including solvent effects with the continuum CPCM method. Results show that, in all cases, ligand binding is mainly driven by dispersion interactions. In addition, ligands with -NH groups display hydrogen bond interactions with CO groups of the peptide strand, increasing the intrinsic affinity toward the β-sheet surface. Solvent effects notably reduce the affinity of charged ThT, as compared to neutral systems, due to its larger solvation energy. As a result, neutral derivatives display significantly higher affinities than ThT in solution, in agreement with exptl. observations. Anal. of the hydrogen bonding network of the β-sheet structure indicates that stacking interactions upon ligand binding induce a shortening of interstrand hydrogen bonding, suggesting a strengthening of the β-sheet.

Journal of Physical Chemistry B 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 In Synthesis of 92-36-4.

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

Schlitzer, Martin published the artcileSynthesis of potential aldose reductase inhibitors based on minimal pharmacophore requirements, Synthetic Route of 92-36-4, the publication is Journal of Pharmacy and Pharmacology (2001), 53(6), 831-839, database is CAplus and MEDLINE.

A series of 17 compounds was synthesized based on the premise that the minimal pharmacophore for aldose reductase inhibition requires the presence of both an aryl group and a polar group connected by a linking structure. Three groups of compounds were synthesized, the first possessing a 4-(6-methyl-2-benzothiazolyl)aniline or 2-aminobenzothiazole group as the aryl group, the second possessing a 2-naphthyl as the aryl group and the third possessing either a 2-phenyl-4-thiazolyl or 5-(2-nitrophenyl)-2-furanyl as the aryl group. In all three of these groups the carboxylate or its Me ester are linked to the aryl group through various lengths of methylene carbons and amide or cinnamide groups. Optimal activity was observed when the carboxyl group was separated from the aryl group by a linking structure of five atoms in length. Both a double bond and an amide moiety are well tolerated in the linking structure.

Journal of Pharmacy and Pharmacology 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, Synthetic Route of 92-36-4.

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

Chung, Byung-Ho published the artcileSynthesis and biological evaluation of new allylamine antimycotics, Category: thiazole, the publication is Yakhak Hoechi (1996), 40(5), 507-512, database is CAplus.

Benzothiazolyl-substituted allylamines were prepared as potential antimycotics. Thus, intermediate Schiff bases, obtained by condensation of 2-aminobenzothiazoles and trans-cinnamaldehyde, were reduced and then methylated to give the benzothiazolyl-substituted allylamines. These compounds, which were tested in vitro against five fungal cell lines containing Trichophyton mentagrophytes, showed no activity in the 0.1-100 μg/mL range.

Yakhak Hoechi 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, Category: thiazole.

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