82632-77-7

Usage

Uses

Used in Pharmaceutical Industry:
4-(4-CHLORO-PHENYL)-5-METHYL-THIAZOL-2-YLAMINE is used as a therapeutic agent for the potential treatment of various diseases, including cancer, neurodegenerative disorders, and diabetes. Its ability to modulate GSK-3 activity makes it a promising candidate for developing novel treatments targeting these conditions.
Used in Cancer Treatment:
In the oncology field, 4-(4-CHLORO-PHENYL)-5-METHYL-THIAZOL-2-YLAMINE is used as an anticancer agent, potentially inhibiting the growth and progression of cancer cells by targeting the GSK-3 enzyme. Its application may contribute to the development of new cancer therapies.
Used in Neurodegenerative Disorder Treatment:
4-(4-CHLORO-PHENYL)-5-METHYL-THIAZOL-2-YLAMINE is used as a neuroprotective agent for the potential treatment of neurodegenerative disorders. Its modulation of GSK-3 activity may help in managing the progression of diseases like Alzheimer's and Parkinson's.
Used in Diabetes Management:
In the field of diabetes, 4-(4-CHLORO-PHENYL)-5-METHYL-THIAZOL-2-YLAMINE is used as a potential therapeutic agent for managing glucose metabolism. Its inhibitory effect on GSK-3 may contribute to the regulation of insulin signaling and glucose homeostasis, offering a new approach to diabetes treatment.

InChI:InChI=1/C10H9ClN2S/c1-6-9(13-10(12)14-6)7-2-4-8(11)5-3-7/h2-5H,1H3,(H2,12,13)

Upstream product

• 6285-05-8 4'-chloropropiophenone 
• 17356-08-0 thiourea 
• 877-37-2 2-bromo-1-(4-chlorophenyl)-1-propanone 
• 333-20-0 potassium thioacyanate 
• 13856-85-4 1-(4-chlorophenyl)-1-propanol 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 103096-90-8 4-acetylamino-N-[4-(4-chloro-phenyl)-5-methyl-thiazol-2-yl]-benzenesulfonamide 
• 1398574-80-5 C₁₅H₁₅ClN₂O₃S 
• 438215-14-6 4-((4-(4-chlorophenyl)-5-methylthiazol-2-yl)amino)-4-oxobutanoic acid 
• 27225-23-6 4-(4-chloro-phenyl)-2-fluoro-5-methyl-thiazole 
• 130831-35-5 4-amino-N-[4-(4-chloro-phenyl)-5-methyl-thiazol-2-yl]-benzenesulfonamide 

Relevant academic research and scientific papers

Synthesis and biological evaluation of novel thiazole- VX-809 hybrid derivatives as F508del correctors by QSAR-based filtering tools

The most common CF mutation, F508del, impairs the processing and gating of CFTR protein. This deletion results in the improper folding of the protein and its degradation before it reaches the plasma membrane of epithelial cells. Present correctors, like VX809 only induce a partial rescue of the mutant protein. Our previous studies reported a class of compounds, called aminoarylthiazoles (AATs), featuring an interesting activity as correctors. Some of them show additive effect with VX809 indicating a different mechanism of action. In an attempt to construct more interesting molecules, it was thought to generate chemically hybrid compounds, blending a portion of VX809 merged to the thiazole scaffold. This approach was guided by the development of QSAR analyses, which were performed based on the F508del correctors so far disclosed in the literature. This strategy was aimed at exploring the key requirements turning in the corrector ability of the collected derivatives and allowed us to derive a predictive model guiding for the synthesis of novel hybrids as promising correctors. The new molecules were tested in functional and biochemical assays on bronchial CFBE41o-cells expressing F508del-CFTR showing a promising corrector activity.

Citric Acid-catalyzed Synthesis of 2,4-Disubstituted Thiazoles from Ketones via C–Br, C–S, and C–N Bond Formations in One Pot: A Green Approach

An improved and greener protocol has been developed for the synthesis of 2,4-disubstituted thiazoles via C–Br, C–S, and, C–N bond formations in a single step from readily available ketones, N-bromosuccinimide (NBS), and thiourea catalyzed by citric acid in a mixture of ethanol and water (3:1) under reflux conditions. This method has the advantages of freedom from the isolation of lachrymatory α-bromoketones, ease of carrying out, cleaner reaction profile, broad substrate scope, freedom from chromatographic purification, and suitability for large-scale synthesis.

Synthesis and antimicrobial activities of some novel 2,3-substituted-1,3-thiazolidin-4-ones derived from 2-amino-1,3-thiazole

New 2,3-substituted-1,3-thiazolidin-4-one (6a-f) were prepared by cyclocondensation of 2-[6-(4-chlorobenzyloxy)-2-naphthyliden]-4-(4-substituted phenyl)-5-methyl-1,3-thiazole (5a-f) and mercaptoacetic acid in benzene. The synthesized compounds were charac

Design, synthesis and biological evaluation of thiazole- and indole-based derivatives for the treatment of type II diabetes

Present studies have shown that the lipid carrier has a significant role in several aspects of metabolic syndrome in A-FABP/ap2-deficient mice, including type 2 diabetes and atherosclerosis. 38 Thiazole- and indole-based derivatives were synthesized and investigated for their inhibitory effects on the production of LPS-stimulated TNF-α. Among them, 12b exhibited an excellent inhibitory efficiency compared to BMS309403 (95% vs. 85%) at the concentration of 10 μM and a binding affinity for ap2 with the apparent Ki values 33 nM. Oral administration of 12b at a dosage of 50 mg/kg effectively reduced the levels of plasma blood glucose, triglycerides, insulin, total cholesterol and alanine aminotransferase in high-fat/diet-induced obesity model. The results highlighted that 12b was a potent anti-diabetic agent.

PYRIMIDINEDIONE-FUSED HETEROCYCLIC COMPOUNDS AS TRPA1 MODULATORS

The present invention is related to novel pyrimidinedione-fused heterocyclic compounds as TRPA (Transient Receptor Potential subfamily A) modulators. In particular, compounds described herein are useful for treating or preventing diseases, conditions and/or disorders modulated by TRPA1 (Transient Receptor Potential subfamily A, member 1). Also provided herein are processes for preparing compounds described herein, intermediates used in their synthesis, pharmaceutical compositions thereof, and methods for treating or preventing diseases, conditions and/or disorders modulated by TRPA1.

QUINAZOLINEDIONE DERIVATIVES AS TRPA1 MODULATORS

The present invention provides Quinazolinedione derivatives as TRPA (Transient Receptor Potential subfamily A) modulators. In particular, compounds described herein are useful for treating or preventing diseases, conditions and/or disorders modulated by T

PHTHALIMIDE DERIVATIVES AS TRPA1 MODULATORS

The present invention provides TRPA (Transient Receptor Potential subfamily A) modulators. In particular, compounds described herein are useful for treating or preventing diseases, conditions and/or disorders modulated by TRPAl (Transient Receptor Potential subfamily A, member 1) modulators. Also provided herein are processes for preparing compounds described herein, intermediates used in their synthesis, pharmaceutical compositions thereof, and methods for treating or preventing diseases, conditions and/or disorders modulated by TRPAl.

One pot synthesis using supported reagents system KSCN/SiO 2-RNH3OAc/Al2O3: Synthesis of 2-aminothiazoles and N-allylthioureas

A simple and efficient method has been developed for the synthesis of 2-aminothiazoles and N-allylthioureas from commercially available materials in one pot by using a supported reagents system, KSCN/SiO2-RNH 3OAc/Al2O3, in which α-halo ketone reacts first KSCN/SiO2 and the product, α-thiocyanatoketone, reacts with RNH3OAc/Al2O3 to give the final product, 2-aminothiazoles, in good yield and allyl bromide reacts with KSCN/SiO 2 and the product, allyl isothiocyanate, reacts with RNH 3OAc/Al2O3 to give N-allylthiourea.

Sulfonylated aminothiazoles as new small molecule inhibitors of protein phosphatases

Based on a previously identified lead structure, SC-ααδ9, we have developed a versatile new chemical scaffold that can be readily modified to generate libraries of both Tyr and dual specificity phosphatase inhibitors with reduced molecular weight and lipophilicity. The most potent analogue identified to date, aminothiazole 8z, inhibits the dual specificity phosphatase Cdc25B with a Ki of 4.6 ± 0.4 μM and a Hill coefficient of 2.

Clean synthesis of α-bromo ketones and their utilisation in the synthesis of 2-alkoxy-2,3-dihydro-2-aryl-1,4-benzodioxanes, 2-amino-4-aryl-1,3-thiazoles and piperidino-2-amino-1,3-thiazoles using polymer-supported reagents

An array of 2-alkoxy-2,3-dihydro-2-aryl-1,4-benzodioxane derivatives and 2-amino-1,3-thiazoles were prepared in high yield using a straightforward three-step and two-step sequence of polymer-supported reagents, respectively and other polymer-supported sequestering reagents without any chromatographic purification step. A key step involves clean and efficient bromination of acetophenones using polymer-supported pyridinium bromide perbromide (PSPBPB) and subsequent cyclisation reaction.