61636-28-0

Usage

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

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

Downstream Products

• 823213-16-7 3-(2-(3,4,5-trimethoxybenzylideneamino)thiazol-4-yl)-2H-chromen-2-one 
• 1233880-59-5 7-phenyl-3-[(3'-coumarinyl)]-5H-[1,3]-thiazolo-[3,2-a]-pyrimidine-5-one 

Relevant academic research and scientific papers

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

A new selective chromogenic and turn-on fluorogenic probe for copper(ii) in solution and vero cells: Recognition of sulphide by [CuL]

A new coumarin-appended thioimidazole-linked imine conjugate, viz. L has been synthesized and characterized. L has been found to recognize Cu2+ selectively among a wide range of biologically relevant metal ions. The chemosensing behavior of L has been demonstrated through fluorescence, absorption, visual fluorescence color changes, ESI-MS and 1H NMR titrations. The chemosensor L showed selectivity toward Cu2+ by switch on fluorescence among the 18 metal ions studied with a detection limit of 1.53 μM. The complex formed between L and Cu2+ is found to be 1:1 on the basis of absorption and fluorescence titrations and was confirmed by ESI-MS. DFT and TDDFT calculations were performed in order to demonstrate the structure of L and [CuL] and the electronic properties of chemosensor L and its copper complex. This highly fluorescent [CuL] complex has been used to recognize sulphide selectively among the other allied anions. Microstructural features of L and its Cu2+ complex have been investigated by SEM imaging (scanning electron microscopy). The biological applications of L were evaluated in Vero cells and it was found to exhibit low cytotoxicity and good membrane permeability for the detection of Cu2+. This journal is

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.

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.

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.

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.

Design, synthesis, antioxidant and anticancer activity of new coumarin derivatives linked with thiazole, isoxazole or pyrazole moiety

Background: Three new series of coumarin derivatives 4a-e, 6a-d and 7a-d were synthesized and characterized by elemental analyses and spectral data including 2D NMR. All compounds 4a-e, 6a-d and 7a-d were evaluated for their in vitro antioxidant and antic

Synthesis, spectroscopic, thermal and electrochemical studies on thiazolyl azo based disperse dyes bearing coumarin

In this study, seven novel thiazolyl azo disperse dyes (6a-g) were synthesized and fully characterized by FT-IR, 1H NMR, 13C NMR, and mass spectral techniques. The electronic absorption spectra of the dyes in solvents of different polarities cover a λmax range of 404-512 nm. The absorption properties of the dyes changed drastically upon acidification. This was due to the protonation of the nitrogen in the thiazole ring, which in turn increased the donor-acceptor interplay of the π system in the dyes, and therefore increased the absorption properties of the prepared dyes. Thermal analysis showed that these dyes are thermal stable up to 269°C. Additionally, the electrochemical behavior of the dyes (6a-g) were investigated using cyclic voltammetric and chronoamperometric techniques, in the presence of 0.10 M tetrabutylammonium tetrafluoroborate, in dimethylsulfoxide, at a glassy carbon electrode. The number of transferred electrons, and the diffusion coefficient were determined by electrochemical methods. The results showed that, for all the dyes, one oxidation peak and two reduction peaks were observed.

3-(5-(Benzylideneamino)thiazol-3-yl)-2H-chromen-2-ones: A new class of alkaline phosphatase and ecto-5′-nucleotidase inhibitors

A new series of 3-(2-(benzylideneamino)thiazol-4-yl)-2H-chromen-2-ones has been synthesized. The structures of the compounds were established by means of 1H and 13C NMR spectroscopy. All compounds were evaluated for their potential t