39893-80-6

Usage

Uses

Used in Pharmaceutical Industry:
4-(3,4-Dichloro-phenyl)-thiazol-2-ylamine is used as a potential pharmaceutical compound for its potential antimicrobial, anti-inflammatory, and anticancer properties. Its unique structural features and biological activities make it a promising candidate for the development of new drugs to treat various diseases.
Used in Agrochemical Industry:
4-(3,4-Dichloro-phenyl)-thiazol-2-ylamine is used as a potential agrochemical compound for its potential antimicrobial properties. It may be utilized in the development of new pesticides or fungicides to protect crops from various pathogens, thereby increasing agricultural productivity.

InChI:InChI=1/C9H6Cl2N2S/c10-6-2-1-5(3-7(6)11)8-4-14-9(12)13-8/h1-4H,(H2,12,13)

Upstream product

• 2632-10-2 2-bromo-1-(3,4-dichlorophenyl)ethanone 
• 17356-08-0 thiourea 
• 2642-63-9 3',4'-dichloroacetophenone 

Downstream Products

• 68301-55-3 4-amino-N-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-benzenesulfonamide 
• 372093-95-3 N-[4-(3,4-Dichlorophenyl)thiazol-2-yl]-(2-chloro-5-nitrophenyl)carboxamide 
• 1366099-15-1 C₁₆H₁₅Cl₃N₆S 
• 560090-53-1 4-((4-(3,4-dichlorophenyl)thiazol-2-yl)amino)-4-oxobutanoic acid 
• 1398574-78-1 C₁₄H₁₂Cl₂N₂O₃S 

Relevant academic research and scientific papers

Solid state thiazole-based fluorophores: Promising materials for white organic light emitting devices

A facile and more efficient solvent-free mechanochemical synthetic route has been developed for the synthesis of a series of solid state white light emissive thiazole-based donor-acceptor (D-A) type fluorophores, 2-(3-pyridyl)/2-aminothiazoles from ω-bromomethylketones and pyridine-3-carbothioamide/thiourea in the presence of silica-supported HClO4 as a reusable solid Br?nsted acid catalyst at RT. The photophysical and electrochemical properties of these compounds have been derived. Most of the studied D-A type solid thiazole-based fluorophores emitted white light and it can be tuned from warm - ideal - cold white light by introduction of a variety of substituents at 4th position of 2-(3-pyridyl)/2-aminothiazoles. Further, HOMO and LUMO energy levels of the titled compounds are found to be in the range ?5.52 eV to ?5.72 eV and ?1.84 eV to ?2.45 eV, respectively. The lifetimes of these levels of thiazole-based fluorophores have been determined through luminescence decay curves and are found to be in the range of 7.7–11 μs. The photophysical and electrochemical properties of the synthesized thiazole-based fluorophores indicate that the compounds could be promising materials for white organic light emitting devices.

GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with a defect in glyoxylate metabolism, for example a disease or disorder associated with the enzyme glycolate oxidase (GO) or alterations in oxalate metabolism. Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.

Identification and Optimization of Novel Small c-Abl Kinase Activators Using Fragment and HTS Methodologies

Abelson kinase (c-Abl) is a ubiquitously expressed, nonreceptor tyrosine kinase which plays a key role in cell differentiation and survival. It was hypothesized that transient activation of c-Abl kinase via displacement of the N-terminal autoinhibitory "myristoyl latch", may lead to an increased hematopoietic stem cell differentiation. This would increase the numbers of circulating neutrophils and so be an effective treatment for chemotherapy-induced neutropenia. This paper describes the discovery and optimization of a thiazole series of novel small molecule c-Abl activators, initially identified by a high throughput screening. Subsequently, a scaffold-hop, which exploited the improved physicochemical properties of a dihydropyrazole analogue, identified through fragment screening, delivered potent, soluble, cell-active c-Abl activators, which demonstrated the intracellular activation of c-Abl in vivo.

GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme glycolate oxidase (GO). Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.

SUBSTITUTED PROPANAMIDES AS INHIBITORS OF NUCLEASES

The invention provides compounds represented by the structural formula (1): wherein R1, R2, R3, R4, R5, R6 are as defined in the claims. The compounds are inhibitors of nucleases, and are useful in particular in a method of treatment and/or prevention of proliferative diseases, neurodegenerative diseases, and other genomic instability associated diseases.

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.

Aminothiazole-featured pirinixic acid derivatives as dual 5-lipoxygenase and microsomal prostaglandin E2 synthase-1 inhibitors with improved potency and efficiency in vivo

Dual inhibition of microsomal prostaglandin E2 synthase-1 (mPGES-1) and 5-lipoxygenase (5-LO) is currently pursued as potential pharmacological strategy for treatment of inflammation and cancer. Here we present a series of 26 novel 2-aminothiaz

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.

Convenient and simple synthesis of 2-aminothiazoles by the reaction of α-halo ketone carbonyls with ammonium thiocyanate in the presence of N-methylimidazole

Substituted 2-aminothiazole derivatives were obtained as a result of N-methylimidazole catalyzed cyclization of α-halo ketone carbonyls with ammonium thiocyanate in water-alcoholic media. The generality of the method has been demonstrated by screening a series of aromatic/heteroaromatic/aliphatic α-halo ketones, α-halo β-diketones, and α-halo β-ketoesters. The developed method is simple, mild, and general route for the preparation of diversely functionalized 2-aminothiazoles in good to moderate yields from readily available starting materials.

An efficient, uncatalyzed, and rapid synthesis of thiazoles and aminothiazoles under microwave irradiation and investigation of their biological activity

A convenient method for the synthesis of thiazoles by treatment of -bromoketones with thioamides (Hantzsch synthesis) in the absence of catalysts under microwave irradiation has been developed. The products were formed rapidly in excellent yields. An efficiency comparison of time, yield, and effort clearly proved the microwave technique to be superior. The structures of the newly synthesized compounds were characterized by spectroscopic data and elemental analyses. The synthesized compounds were tested for their biological activity. Depending on the substituents, some of the thiazoles exhibit very good antibacterial or antifungal activity.