61636-28-0

Basic information

• Product Name: 3-(2-AMINO-1,3-THIAZOL-4-YL)-2H-CHROMEN-2-ONE HYDROBROMIDE
• Synonyms: 3-(2-Aminothiazol-4-yl)coumarin
• CAS NO: 61636-28-0
• Molecular Formula: C₁₂H₈N₂O₂S
• Molecular Weight: 244.27
• Mol File: 61636-28-0.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 511.7°Cat760mmHg
• Flash Point: 263.2°C
• Appearance: /
• Density: 1.487g/cm³
• Vapor Pressure: 1.39E-10mmHg at 25°C
• Refractive Index: 1.72
• CAS DataBase Reference: 3-(2-AMINO-1,3-THIAZOL-4-YL)-2H-CHROMEN-2-ONE HYDROBROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-AMINO-1,3-THIAZOL-4-YL)-2H-CHROMEN-2-ONE HYDROBROMIDE(61636-28-0)
• EPA Substance Registry System: 3-(2-AMINO-1,3-THIAZOL-4-YL)-2H-CHROMEN-2-ONE HYDROBROMIDE(61636-28-0)

Safety Data

• Hazardous Substances Data: 61636-28-0(Hazardous Substances Data)

Usage

Description

3-(2-AMINO-1,3-THIAZOL-4-YL)-2H-CHROMEN-2-ONE HYDROBROMIDE is a chemical compound characterized by its unique molecular structure, which features a 2H-chromen-2-one core with a 2-amino-1,3-thiazol-4-yl group attached at the 3-position. 3-(2-AMINO-1,3-THIAZOL-4-YL)-2H-CHROMEN-2-ONE HYDROBROMIDE is of interest due to its potential applications in various fields, particularly in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
3-(2-AMINO-1,3-THIAZOL-4-YL)-2H-CHROMEN-2-ONE HYDROBROMIDE is used as a key intermediate for the synthesis of histone deacetylase inhibitors with antifibrotic activity. These inhibitors play a crucial role in modulating gene expression and have potential therapeutic applications in treating fibrosis-related diseases.
Used in Research and Development:
In the field of research and development, 3-(2-AMINO-1,3-THIAZOL-4-YL)-2H-CHROMEN-2-ONE HYDROBROMIDE serves as a valuable compound for exploring its chemical properties, reactivity, and potential interactions with other molecules. This can lead to the discovery of new drug candidates and therapeutic strategies.
Used in Chemical Synthesis:
3-(2-AMINO-1,3-THIAZOL-4-YL)-2H-CHROMEN-2-ONE HYDROBROMIDE can be utilized as a building block in the synthesis of various complex organic molecules, including those with potential biological activities. Its unique structure makes it an attractive candidate for the development of novel compounds with diverse applications.

InChI:InChI=1/C12H8N2O2S/c13-12-14-9(6-17-12)8-5-7-3-1-2-4-10(7)16-11(8)15/h1-6H,(H2,13,14)

Upstream product

• 29310-88-1 3-bromoacetylcoumarin 
• 17356-08-0 thiourea 
• 3949-36-8 3-acetylcoumarin 
• 90-02-8 salicylaldehyde 
• 176788-59-3 3-(2-chloro-thiazol-4-yl)-coumarin 
• 141099-74-3 3-(2-thiocyanatoacetyl)-2H-1-benzopyran-2-one 

Downstream Products

• 128404-91-1 3-(2-(((2-hydroxy-3,5-dibromophenyl)methylene)amino)-4-thiazolyl)-2H-1-benzopyran-2-one 
• 128404-90-0 3-(2-(((2-hydroxy-3-bromophenyl)methylene)amino)-4-thiazolyl)-2H-1-benzopyran-2-one 
• 128404-92-2 3-(2-(((p-methoxyphenyl)methylene)amino)-4-thiazolyl)-2H-1-benzopyran-2-one 
• 128404-88-6 3-(2-(((2-hydroxyphenyl)methylene)amino)-4-thiazolyl)-2H-1-benzopyran-2-one 
• 128404-89-7 3-(2-(((2-hydroxy-3-methoxyphenyl)methylene)amino)-4-thiazolyl)-2H-1-benzopyran-2-one 
• 87503-74-0 2-chloro-N-[4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl]acetamide 
• 128404-93-3 3-(2-((p-(N,N-dimethylamino)phenylmethylene)amino)-4-thiazolyl)-2H-1-benzopyran-2-one 
• 848903-46-8 3-(2-{[1-(5-Chloro-2-hydroxy-phenyl)-meth-(E)-ylidene]-amino}-thiazol-4-yl)-chromen-2-one 
• 339283-32-8 3-(2-{[1-(5-Bromo-2-hydroxy-phenyl)-meth-(E)-ylidene]-amino}-thiazol-4-yl)-chromen-2-one 
• 1233880-59-5 7-phenyl-3-[(3'-coumarinyl)]-5H-[1,3]-thiazolo-[3,2-a]-pyrimidine-5-one 
• 1352563-68-8 3-(4-hydroxy-3-methyl-1-phenyl-1,4-dihydropyrazolo[4,3-e]thiazolo[3,2-a]pyrimidin-8-yl)-2H-chromen-2-one 

Relevant articles and documents

Solution-phase synthesis of a combinatorial library of 3-[4-(coumarin-3-yl) -1,3-thiazol-2-ylcarbamoyl]propanoic acid amides

The parallel solution-phase synthesis of a new combinatorial library of 3-[4-(R1-coumarin-3-yl)-1,3-thiazol-2-ylcarbamoyl]propanoic acid amides 9 has been developed. The synthesis involves two steps: 1) the synthesis of core building blocks - 3-[4-(coumar

Novel fluorescent coumarin-thiazole based sensors for selective determination of cyanide in aqueous media

Novel colorimetric and fluorimetric fluorescent coumarin-thizole based chemosensors 4a-b were synthesized and characterized using spectroscopic methods. The photophysical properties of the sensors were determined in six solvents by UV–Vis and fluorosence spectrometers. The sensitivity and selectivity of 4a-b towards anions were investigated by absorption, emission and naked-eye detection methods in organic and aqueous media. Both sensors 4a-b showed selectivity to detecting of CN? besides other interference anions (F?, AcO? and H2PO4?) in aqueous solution. The sensing mechanism of the sensors were investigated by reversibility and 1H NMR titration studies and also supported by DFT calculations. Moreover, LOD values of 4a-b were calculated and the results can be used to detect CN? at a concentration lower than the WHO guideline (2.7 mM) for cyanide. Thermal studies of the compounds have shown that the 4a-b have enough thermal stability properties for application as optic dye. The compound 4b was fully spectroscopically characterized and its structure was unambiguously determined by single crystal X-ray crystallography.

Synthesis and biological evaluation of novel thiazolyl-coumarin derivatives as potent histone deacetylase inhibitors with antifibrotic activity

New histone deacetylases (HDAC) inhibitors with low toxicity to non-cancerous cells, are a prevalent issue at present because these enzymes are actively involved in fibrotic diseases. We designed and synthesized a novel series of thiazolyl-coumarins, substituted at position 6 (R = H, Br, OCH3), linked to classic zinc binding groups, such as hydroxamic and carboxylic acid moieties and alternative zinc binding groups such as disulfide and catechol. Their in vitro inhibitory activities against HDACs were evaluated. Disulfide and hydroxamic acid derivatives were the most potent ones. Assays with neonatal rat cardiac fibroblasts demonstrated low cytotoxic effects for all compounds. Regarding the parameters associated to cardiac fibrosis development, the compounds showed antiproliferative effects, and triggered a strong decrease on the expression levels of both α-SMA and procollagen I. In conclusion, the new thiazolyl-coumarin derivatives inhibit HDAC activity and decrease profibrotic effects on cardiac fibroblasts.

Design, synthesis and docking study of novel coumarin ligands as potential selective acetylcholinesterase inhibitors

New coumaryl-thiazole derivatives with the acetamide moiety as a linker between the alkyl chains and/or the heterocycle nucleus were synthesized and in vitro tested as acetylcholinesterase (AChE) inhibitors. 2-(diethylamino)-N-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)acetamide (6c, IC50 value of 43 nM) was the best AChE inhibitor with a selectivity index of 4151.16 over BuChE. Kinetic study of AChE inhibition revealed that 6c was a mixed-type inhibitor. Moreover, the result of H4IIE hepatoma cell toxicity assay for 6c showed negligible cell death. Molecular docking studies were also carried out to clarify the inhibition mode of the more active compounds. Best pose of compound 6c is positioned into the active site with the coumarin ring wedged between the residues of the CAS and catalytic triad of AChE. In addition, the coumarin ring is anchored into the gorge of the enzyme by H-bond with Tyr130.