17228-98-7

Basic information

• Product Name: 2-(4-CHLOROPHENYL)-1,3-THIAZOLE-4-CARBOXYLIC ACID
• Synonyms: BUTTPARK 99\50-64;2-(4-CHLORO-PHENYL)-THIAZOLE-4-CARBOXYLIC ACID;2-(4-CHLOROPHENYL)-1,3-THIAZOLE-4-CARBOXYLIC ACID;2-(4-Chlorophenyl)-1,3-thiazole-4-carboxylic acid, 97+%
• CAS NO: 17228-98-7
• Molecular Formula: C₁₀H₆ClNO₂S
• Molecular Weight: 239.68
• Mol File: 17228-98-7.mol

Chemical Properties

• Melting Point: 187-190°C
• Boiling Point: 441.9 °C at 760 mmHg
• Flash Point: 221 °C
• Appearance: /
• Density: 1.48 g/cm³
• Vapor Pressure: 1.38E-08mmHg at 25°C
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(4-CHLOROPHENYL)-1,3-THIAZOLE-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-CHLOROPHENYL)-1,3-THIAZOLE-4-CARBOXYLIC ACID(17228-98-7)
• EPA Substance Registry System: 2-(4-CHLOROPHENYL)-1,3-THIAZOLE-4-CARBOXYLIC ACID(17228-98-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 17228-98-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-Chlorophenyl)-1,3-thiazole-4-carboxylic acid is used as an intermediate in the synthesis of pharmaceuticals for its potential biological activity. 2-(4-CHLOROPHENYL)-1,3-THIAZOLE-4-CARBOXYLIC ACID's antimicrobial and anticancer properties make it a promising candidate for the development of new drugs targeting various diseases and infections.
Used in Agrochemical Industry:
2-(4-Chlorophenyl)-1,3-thiazole-4-carboxylic acid is also used as an intermediate in the synthesis of agrochemicals. Its biological activity can be harnessed to develop novel compounds for agricultural applications, such as pesticides or herbicides, to improve crop protection and yield.
Used in Drug Development:
2-(4-Chlorophenyl)-1,3-thiazole-4-carboxylic acid is used as a building block in drug development due to its unique chemical structure and functional groups. The chlorophenyl and carboxylic acid groups allow for the creation of new bioactive compounds with potential therapeutic applications in various medical fields.

InChI:InChI=1/C10H6ClNO2S/c11-7-3-1-6(2-4-7)9-12-8(5-15-9)10(13)14/h1-5H,(H,13,14)/p-1

Upstream product

• 61786-00-3 ethyl 2-(4-chlorophenyl)thiazole-4-carboxylate 
• 40361-62-4 4-chloromethyl-2-(4-chloro-phenyl)-4,5-dihydro-thiazol-4-ol 
• 1315510-11-2 methyl 2-(4-chlorophenyl)thiazole-4-carboxylate 
• 86264-82-6 (4R)-methyl 2-(4-chlorophenyl)-1,3-thiazolidine-4-carboxylate 
• 1113-59-3 bromopyruvic acid 
• 2521-24-6 4-chlorothiobenzamide 
• 1679-18-1 4-Chlorophenylboronic acid 
• 36093-99-9 [2-(4-chloro-phenyl)-thiazol-4-yl]-methanol 

Downstream Products

• 65823-92-9 1-[2-(4-chloro-phenyl)-thiazol-4-yl]-ethanone 
• 57677-86-8 2-chloro-1-[2-(4-chloro-phenyl)-thiazol-4-yl]-ethanone 
• 104106-86-7 2-(4-chlorophenyl)-4-thiazolecarboxylic acid chloride 
• 57677-82-4 1-[2-(4-chloro-phenyl)-thiazol-4-yl]-2-diazo-ethanone 

Relevant articles and documents

Identification of BR102910 as a selective fibroblast activation protein (FAP) inhibitor

Fibroblast activation protein (FAP) belongs to the family of prolyl-specific serine proteases and displays both exopeptidase and endopeptidase activities. FAP expression is undetectable in most normal adult tissues, but is greatly upregulated in sites of tissue remodeling, which include fibrosis, inflammation and cancer. Due to its restricted expression pattern and dual enzymatic activities, FAP inhibition is investigated as a therapeutic option for several diseases. In the present study, we described the structure–activity relationship of several synthesized compounds against DPPIV and prolyl oligopeptidase (PREP). In particular, BR102910 (compound 24) showed nanomolar potency and high selectivity. Moreover, the in vivo FAP inhibition study of BR102910 (compound 24) using C57BL/6J mice demonstrated exceptional profiles and satisfactory FAP inhibition efficacy. Based on excellent in vitro and in vivo profiles, the potential of BR102910 (compound 24) as a lead candidate for the treatment of type 2 diabetes is considered.

Purple acid phosphatase inhibitors as leads for osteoporosis chemotherapeutics

Purple acid phosphatases (PAPs) are metalloenzymes that catalyse the hydrolysis of phosphate esters under acidic conditions. Their active site contains a Fe(III)Fe(II) metal centre in mammals and a Fe(III)Zn(II) or Fe(III)Mn(II) metal centre in plants. In humans, elevated PAP levels in serum strongly correlate with the progression of osteoporosis and metabolic bone malignancies, which make PAP a target suitable for the development of chemotherapeutics to combat bone ailments. Due to difficulties in obtaining the human enzyme, the corresponding enzymes from red kidney bean and pig have been used previously to develop specific PAP inhibitors. Here, existing lead compounds were further elaborated to create a series of inhibitors with Ki values as low as ～30 μM. The inhibition constants of these compounds were of comparable magnitude for pig and red kidney bean PAPs, indicating that relevant binding interactions are conserved. The crystal structure of red kidney bean PAP in complex with the most potent inhibitor in this series, compound 4f, was solved to 2.40 ? resolution. This inhibitor coordinates directly to the binuclear metal centre in the active site as expected based on its competitive mode of inhibition. Docking simulations predict that this compound binds to human PAP in a similar mode. This study presents the first example of a PAP structure in complex with an inhibitor that is of relevance to the development of anti-osteoporotic chemotherapeutics.

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A catch-and-release strategy for the combinatorial synthesis of 4-acylamino-1,3-thiazoles as potential CDK5 inhibitors

Two-dimensional libraries of 4-acylamino-1,3-thiazoles 9 were prepared via Curtius rearrangement of 1,3-thiazole-4-carbonyl azides 6, trapping of the intermediate isocyanates with oxime resin, and thermal regeneration of the isocyanates from the washed resin in the presence of nucleophiles. Several compounds proved to be selective inhibitors of CDK5/p25 versus the closely homologous CDK2/cyclin A enzyme, with the best analogue (43) possessing over 100-fold selectivity.