21344-90-1

Usage

Uses

Used in Pharmaceutical Industry:
4-(2-CHLORO-PHENYL)-THIAZOL-2-YLAMINE is used as a building block in the synthesis of various pharmaceuticals for its potential antibacterial, antifungal, and antiviral properties. It serves as an important candidate for the development of new drugs, contributing to the advancement of medical treatments and therapies.
Used in Agrochemical Industry:
In the agrochemical sector, 4-(2-CHLORO-PHENYL)-THIAZOL-2-YLAMINE is utilized as a precursor in the synthesis of compounds with pesticidal properties. Its application aids in the development of effective and environmentally friendly solutions for crop protection and disease management.
Used in Organic Synthesis:
4-(2-CHLORO-PHENYL)-THIAZOL-2-YLAMINE is employed as a versatile precursor in the synthesis of other important compounds. Its unique structure and functional groups make it a valuable component in the creation of a wide range of organic compounds, further expanding its applications across various industries.

InChI:InChI=1/C9H7ClN2S/c10-7-4-2-1-3-6(7)8-5-13-9(11)12-8/h1-5H,(H2,11,12)

Upstream product

• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 17356-08-0 thiourea 
• 673477-11-7 4-(2-chlorophenyl)thiazol-2-amine hydrobromide 
• 5000-66-8 2-chlorophenacyl bromide 
• 609-65-4 o-chlorobenzoyl chloride 
• 3900-89-8 2-Chlorobenzeneboronic acid 

Downstream Products

• 153776-97-7 [4-(2-Chloro-phenyl)-thiazol-2-yl]-dithiocarbamic acid methyl ester 
• 528583-97-3 5-(4-acetylphenylazo)-2-amino-4-(2-chlorophenyl)thiazole 
• 376349-50-7 N-[4-(2-chlorophenyl)-1,3-thiazol-2-yl][1,1'-biphenyl]-4-sulfonamide 
• 376349-72-3 4,5-Dichloro-N-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]-2-thiophenesulfonamide 
• 376349-32-5 N-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]-4-propylbenzenesulfonamide 
• 376349-67-6 2,3,4-Trichloro-N-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]benzenesulfonamide 
• 376349-38-1 3-Chloro-N-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide 
• 376349-44-9 2,4,6-Trichloro-N-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]benzenesulfonamide 
• 376349-63-2 2,4-Dichloro-N-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]-6-methylbenzenesulfonamide 
• 1229380-22-6 (R)-tert-butyl 3-benzyl-4-(4-(2-chlorophenyl)thiazol-2-ylamino)-4-oxobutanoate 
• 904771-57-9 4-((4-(2-chlorophenyl)thiazol-2-yl)amino)-4-oxobutanoic acid 
• 376349-77-8 3-Bromo-5-chloro-N-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]-2-thiophenesulfonamide 
• 528584-13-6 2-amino-4-(2-chlorophenyl)-5-[4-(4-nitrocinnamoyl)phenylazo]thiazole 

Relevant academic research and scientific papers

A 4-(o-chlorophenyl)-2-aminothiazole: Microwave assisted synthesis, spectral, thermal, XRD and biological studies

A 4-(o-chlorophenyl)-2-aminothiazole (CPAT) has been synthesized by reacting o-chloroacetophenone, iodine and thiourea under microwave irradiation as a green chemistry approach. The reactions proceed selectively and within a couple of minutes giving high

A one-pot synthesis of 2-aminothiazoles via the coupling of ketones and thiourea using I2/dimethyl sulfoxide as a catalytic oxidative system

A series of 2-aminothiazoles is prepared in moderate-to-good yields by the direct coupling of ketones and thiourea using I2/dimethyl sulfoxide as a catalytic oxidative system. This method avoids the preparation of lachrymatory and toxic α-haloketones and the use of an acid-binding agent, thus providing a more convenient approach to 2-aminothiazoles compared to the Hantzsch reaction.

COLLAGEN 1 TRANSLATION INHIBITORS AND METHODS OF USE THEREOF

The present invention relates to novel collagen translation inhibitors 1, a composition, their preparation methods, and their uses for the treatment of fibrosis in particular, fibrosis of the lung, liver, kidney, cardiac and dermal fibrosis, IPF, wound he

Synthesis of 2-aminothiazoles via rhodium-catalyzed carbenoid insertion/annulation of sulfoxonium ylides with thioureas

Sulfoxonium ylides as carbene precursors couple smoothly with thioureas in the presence of 5 mol% of rhodium(II) acetate dimmer via carbenoid insertion to afford the corresponding 2-aminothiazoles with high chemoselectivity, providing a facile and efficient approach to access a variety of 2-aminothiazole derivatives with good functional groups tolerance.

Method for preparing 2-aminothiazole compound

The invention discloses a method for preparing a 2-aminothiazole compound. The method comprises the following steps: in an organic solvent, carrying out a condensation reaction on thiourea representedby a formula (II) and a ketone compound represented by a formula (III) at 50-120 DEG C for 6-24 h under the catalysis of elemental iodine, and after the reaction is finished, carrying out post-treatment on the reaction solution to obtain the 2-aminothiazole compound represented by a formula (I). According to the invention, the method has characteristics of cheap and easily available reaction rawmaterials, mild reaction conditions, simpleness, no requirement of transition metal catalysts and a stoichiometric halogenating reagents and cost reducing, and can be used for synthesizing a series of2-aminothiazole derivatives, and the prepared products can be used as important intermediates for synthesizing thiazole structure-containing drugs or bioactive compounds.

Structure-Based Design of N-(5-Phenylthiazol-2-yl)acrylamides as Novel and Potent Glutathione S-Transferase Omega 1 Inhibitors

Using reported glutathione S-transferase omega 1 (GSTO1-1) cocrystal structures, we designed and synthesized acrylamide-containing compounds that covalently bind to Cys32 on the catalytic site. Starting from a thiazole derivative 10 (GSTO1-1 IC50 = 0.6 μM), compound 18 was synthesized and cocrystallized with GSTO1. Modification on the amide moiety of hit compound 10 significantly increased the GSTO1-1 inhibitory potency. We solved the cocrystal structures of new derivatives, 37 and 44, bearing an amide side chain bound to GSTO1. These new structures showed a reorientation of the phenyl thiazole core of inhibitors, 37 and 44, when compared to 18. Guided by the cocrystal structure of GSTO1:44, analogue 49 was designed, resulting in the most potent GSTO1-1 inhibitor (IC50 = 0.22 ± 0.02 nM) known to date. We believe that our data will form the basis for future studies of developing GSTO1-1 as a new drug target for cancer therapy.

Novel 1,3,5-triazine derivatives exert potent anti-cervical cancer effects by modulating Bax, Bcl2 and Caspases expression

This study aimed to develop novel 1,3,5-triazine derivatives as potent anti-cervical cancer agents. The compounds were synthesized in short steps with an excellent yield and characterized via various spectroscopic and analytical methods. A structure–activity relationship study suggested that electron-withdrawing substituents showed greater anticancer activity than electron-donating groups. Compound 7p (p-fluoro) showed the highest activity against cervical cancer cells. In a nude mouse xenograft model inoculated with HeLa cells, 7p showed dose-dependent inhibition of cervical tumour growth. Histopathological examination of excised tumour-bearing tissues showed that 7p improved the microstructure in a dose-dependent manner. Compound 7p also increased the proportions of HeLa cells in G0/G1 and S-phase and significantly decreased that of G2/M-phase. The effects of 7p on C-caspase-3, C-caspase-9, Bcl-2 and Bax expression in HeLa cells were also determined.

Design and development of some thiazole-based flavanoids as novel antibacterial against pathogens causing surgical site infection for possible benefit in bone trauma via inhibition of DNA gyrase

In this study, a novel class of hybrid thiazole-based flavanoid derivatives were synthesized and characterized by FT-IR, 1H-NMR, 13C-NMR, mass and elemental analysis. These derivatives were evaluated for antibacterial activity for possible benefit in bone trauma via inhibition of DNA gyrase enzyme. Results suggested that compounds 9n, 9o, and 9p showed considerable inhibition of DNA gyrase with considerable activity against tested forty strains of Staphylococcus aureus clinical isolates. Moreover, compound 9n showed hydrogen bonding with LYS460 along with low binding free energy of ?4.36?kcal/mol against DNA gyrase enzyme. The hemolytic activity of the potent compounds showed mild to no activity together with excellent pharmacokinetics, suggesting to have a potential for the development of designed compounds as novel antibacterial agents.

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.

Discovery of novel N-(5-(arylcarbonyl)thiazol-2-yl)amides and N-(5-(arylcarbonyl)thiophen-2-yl)amides as potent RORγt inhibitors

Novel series of N-(5-(arylcarbonyl)thiazol-2-yl)amides and N-(5-(arylcarbonyl)thiophen-2-yl)amides were discovered as potent retinoic acid receptor-related orphan receptor-gamma-t (RORγt) inhibitors. SAR studies of the RORγt HTS hit 6a led to identification of thiazole ketone amide 8h and thiophene ketone amide 9g with high binding affinity and inhibitory activity of Th17 cell differentiation. Compound 8h showed in vivo efficacy in both mouse experimental autoimmune encephalomyelitis (EAE) and collagen induced arthritis (CIA) models via oral administration.