90533-23-6

Usage

Uses

Used in Pharmaceutical Industry:
4-(3-Chloro-phenyl)-thiazol-2-ylamine is used as a building block for the synthesis of various pharmaceutical compounds due to its unique chemical structure and potential biological activities. Its ability to be incorporated into the development of new drugs makes it a valuable intermediate in medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical field, 4-(3-Chloro-phenyl)-thiazol-2-ylamine serves as an intermediate in the production of crop protection chemicals. Its potential to contribute to the development of effective and safe agrochemicals for pest and disease control highlights its importance in this industry.
4-(3-Chloro-phenyl)-thiazol-2-ylamine's properties and potential applications underscore its significance for further exploration and research, with the aim of harnessing its capabilities to address various challenges in healthcare and agriculture.

Upstream product

• 17356-08-0 thiourea 
• 99-02-5 3'-Chloroacetophenone 
• 2039-85-2 3-Chlorostyrene 
• 618-46-2 m-Chlorobenzoyl chloride 
• 620-16-6 3-chloroethylbenzene 
• 41011-01-2 2-bromo-1-(3-chloro-phenyl)-ethanone 

Downstream Products

• 1391979-85-3 N-(4-(3-chlorophenyl)-5-((2-chlorophenyl)(methyl)amino)thiazol-2-yl)-2-(4-(ethylsulfonyl)phenyl)acetamide 
• 1391979-86-4 N-(4-(3-chlorophenyl)-5-(2-isopropylphenoxy)thiazol-2-yl)-2-(4-(ethylsulfonyl)phenyl)acetamide 
• 1391979-87-5 N-(4-(3-chlorophenyl)-5-(4-methoxyphenoxy)thiazol-2-yl)-2-(4-(ethylsulfonyl)phenyl)acetamide 
• 1391979-66-0 N-(5-(4-chlorophenoxy)-4-(3-chlorophenyl)thiazol-2-yl)-2-(4-(ethylsulfonyl)phenyl)acetamide 
• 1391980-02-1 5-bromo-4-(3-chlorophenyl)thiazol-2-amine 
• 1391980-03-2 5-(4-chlorophenoxy)-4-(3-chlorophenyl)thiazol-2-amine 
• 1391979-68-2 N-(5-(2-chlorophenoxy)-4-(3-chlorophenyl)thiazol-2-yl)-2-(4-(ethylsulfonyl)phenyl)acetamide 
• 1391980-04-3 5-(2-chlorophenoxy)-4-(3-chlorophenyl)thiazol-2-amine 
• 1391979-69-3 N-(4-(3-chlorophenyl)-5-phenoxythiazol-2-yl)-2-(4-(ethylsulfonyl)phenyl)acetamide 
• 1391980-05-4 4-(3-chlorophenyl)-5-phenoxythiazol-2-amine 

Relevant academic research and scientific papers

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.

Novel synthesis of 2-Aminothiazoles via Fe(III)-Iodine-catalyzed Hantzsch-type condensation

A novel iron-iodine catalyzed one pot synthesis of 2-aminothiazoles from methyl aryl ketones and thiourea is demonstrated. This protocol can be considered as a catalyzed version of the classical Hantzsch aminothiazole synthesis as it enables the in situ generation of α-iodoketones in the reaction medium using catalytic amount of iodine leading to Hantzsch condensation with thiourea. The supply of iodine for multiple catalytic cycles is ensured by using catalytic amounts of iron as it enables iodide to iodine oxidation. The generality of this protocol is also well established in this manuscript by synthesizing a variety of 2-aminothiazoles from different ketones and thiourea.

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.

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.

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.

Method of synthesizing 2-aminothiazole ring compound from ethylbenzene compound

The invention discloses a method of synthesizing 2-aminothiazole ring compound from ethylbenzene compound, and belongs to the technical field of thiazole ring derivative synthesis. The technical scheme of the invention is characterized by adding the ethylbenzene compound, a phase transfer catalyst, N-bromosuccinimide (NBS) and azodiisobutyronitrile (AIBN) into water in sequence, reacting at 60 DEGC, cooling after the reaction, adding inorganic base and a thiourea compound, and reacting at 80 DEG C to obtain the target product. The synthesis method has the advantages of high yield, mild reaction, low cost and environment friendliness.

Method for synthesizing novel 2-aminothiazole ring derivatives

The invention discloses a method for synthesizing 2-aminothiazole ring derivatives and belongs to the technical field of organic synthesis. The method comprises that an ethylbenzene compound, dibromohydantoin DBH and t-butyl hydroperoxide TBHP are sequentially added to water, the solution undergoes a reaction at 60 DEG C, the reaction product is cooled, an inorganic base and a thiourea compound are orderly added into the reaction product and the mixture undergoes a reaction at 80 DEG C to produce desired product 2-aminothiazole ring derivatives. The method has the advantages of high yield, mild reaction, low cost and environmental friendliness.

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.

Synthesis of 2-aminothiazoles from styrene derivatives mediated by 1,3-dibromo-5,5-dimethylhydrantoin (DBH)

An efficient procedure for the synthesis of 2-aminothiazoles via DBH-mediated oxidative cyclization of styrenes and thioureas is reported. Various alkenes were successfully transformed to the corresponding 2-aminothiazoles in yields of 10–81% via a two-step one-pot manner using DBH as both the bromine source and oxidant. The method can be readily carried out in gram-scale and successfully applied to the synthesis of anti-inflammatory drug fanetizole using styrene as starting material.