2373-31-1

Usage

Uses

Used in Pharmaceutical Synthesis:
6-HYDROXY-4-METHYLCOUMARIN is used as an intermediate in the synthesis of pharmaceutical drugs due to its unique chemical properties and potential therapeutic effects.
Used in Biological Research:
6-HYDROXY-4-METHYLCOUMARIN is used as a fluorescent probe in biological research, allowing for the visualization and study of various biological processes.
Used in Cancer Treatment:
6-HYDROXY-4-METHYLCOUMARIN is used as a potential therapeutic agent for cancer treatment, given its anticoagulant and antioxidant properties, which may contribute to the inhibition of tumor growth and progression.
Used in Inflammation Management:
6-HYDROXY-4-METHYLCOUMARIN is used as an anti-inflammatory agent, potentially helping to reduce inflammation in various medical conditions.
Used in Cardiovascular Disease Prevention:
6-HYDROXY-4-METHYLCOUMARIN is used as a preventive measure for cardiovascular diseases, leveraging its anticoagulant properties to reduce the risk of blood clot formation and associated complications.

InChI:InChI=1/C10H8O3/c1-6-4-10(12)13-9-3-2-7(11)5-8(6)9/h2-5,11H,1H3

Upstream product

• 141-97-9 ethyl acetoacetate 
• 123-31-9 hydroquinone 
• 490-78-8 2,5-Dihydroxyacetophenone 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 6160-80-1 4-methylumbelliferyl-β-D-glucuronide 
• 6295-35-8 6-methoxy-4-methyl-chromen-2-one 
• 150-76-5 4-methoxy-phenol 
• 90207-15-1 4-methyl-6-allyloxycoumarin 
• 607-71-6 4-methyl-2H-chromen-2-one 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 7664-93-9 sulfuric acid 
• 75-77-4 chloro-trimethyl-silane 
• 105-45-3 acetoacetic acid methyl ester 
• 1205-91-0 benzene-1,4-diyl diacetate 

Downstream Products

• 6295-35-8 6-methoxy-4-methyl-chromen-2-one 
• 57707-19-4 3-(2,5-dihydroxy-phenyl)-crotonic acid 
• 93327-45-8 5-[(2,4-dinitro-phenylhydrazono)-methyl]-6-hydroxy-4-methyl-coumarin 
• 262591-13-9 6-ethoxy-4-methylcoumarin 
• 70846-43-4 6-(2-bromoethoxy)-4-methylcoumarin 

Relevant academic research and scientific papers

N-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)thiosemicarbazones of 6-alkoxy-2-oxo-2H-chromene-4-carbaldehydes: synthesis, evaluation of their antibacterial, anti-MRSA, antifungal activity, and docking study

Reaction of 6-alkoxy-2-oxo-2H-chromen-4-carbaldehydes with N-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)thiosemicarbazide yielded corresponding thiosemicarbazones having 2H-chromen-2-one ring. In vitro evaluations showed that these 2H-chromen-2-one compounds exhibited remarkable antibacterial and antifungal activities against some typical bacteria and fungi. Representative compounds with MIC values of 0.78 ? 1.56 μg/mL were 6c, 6g (against S. aureus), 6a, 6f (against S. epidermidis) (Gram-positive bacterial strains), 6e, 6g (against E. coli), 6b, 6e (against K. pneumoniae), and 6d–f (against S. typhimurium) (Gram-negative bacterial strains). Almost all thiosemicarbazones 6a–g had no activity against Gram-positive bacterial strain B. subtilis at these MIC values. Some compounds had strong inhibitory activity against several bacteria, such as 6b (for K. pneumoniae and S. typhimurium), 6d, 6e (for E. coli, K. pneumoniae, and S. typhimurium), 6f (for S. aureus, E. coli, and S. typhimurium), and 6g (for B. subtilis, S. aureus, E. coli, and K. pneumoniae). Some compounds had remarkable inhibitory activity against three clinical MRSA isolates with MIC values of 0.78–6.25 μg/mL. Docking study showed that compound 6g is compatible with the active site of S. aureus DNA gyrase 2XCT, which suggested that the tested compounds inhibited the synthesis of this enzyme. [Figure not available: see fulltext.]

N-Doped Carbon Wrapped Polyoxometalate Derived from POM-IL Hybrid: A Heterogeneous Catalyst for the Synthesis of Coumarin Derivatives under Solvent-Free Conditions

Vanadium substituted Keggin type polyoxometalate loaded N-doped carbon was prepared from polyoxometalate ionic liquid hybrid by carbonization process. The decomposition of organic part generates various functional groups leaving polyoxometalate part intact. The catalyst was characterized by elemental analysis, FTIR, MAS 13C NMR, XPS and electron microscopy studies. The presence of carboxylic acids, aromatic and hetero-aromatic groups in the catalyst was confirmed by 13C NMR. The high resolution C1s and O1s XPS analysis further confirmed the presence of these groups. Various oxidation states of nitrogen were confirmed by deconvoluted N1s XPS spectra. Pyridine adsorption study confirms the presence of Bronsted and Lewis acid sites in the catalyst. Layered structure of the catalyst was confirmed by HR TEM analysis. The hybrid material displayed excellent catalytic activity towards the synthesis of coumarin derivatives under solvent-free conditions.

A highly selective chemosensor for naked-eye sensing of nanomolar Cu(II) in an aqueous medium

A novel highly selective and sensitive colorimetric chemosensor L for the detection of Cu2+ ion with a fast response time was designed and synthesized. Receptor L detected Cu2+ ion by changing its color from colorless to magenta in a semi-aqueous solution. The limit of detection for Cu2+ was calculated to be as low as 28 nM. The possible binding mode of compound L with Cu2+ ion was studied using the Job's method, HRMS, FTIR spectroscopy and 1H NMR spectroscopy titration. Importantly, test strips containing L were fabricated as a naked-eye indicator for Cu2+ ion in pure water samples.

Synthesis of 6- and 7-alkoxy-4-methylcoumarins from corresponding hydroxy coumarins and their conversion into 6- and 7-alkoxy-4-formylcoumarin derivatives

Hydroxy derivatives of 4-methyl-2H-chromen-2-one were prepared from hydroquinone and resorcinol through their reaction with ethyl acetoacetate. These hydroxy coumarins were then converted into corresponding alkoxy derivatives by reaction with alkyl halides. The yields of 6- and 7-alkoxy-4-methylcoumarins 3a–i and 4a–i were 55?95%. Oxidation of these compounds by selenium dioxide under conventional and microwave-assisted heating conditions produced corresponding 4-formyl compounds 5b–h and 6b–h with yields of 40?67% and 90?93%, respectively. Several 6- and 7-alkoxy-4-methylcoumarins 3a–i, 4a–i and nearly all 6- and 7-alkoxy-4-formylcoumarins 5b–h, 6b–h are novel compounds.

Synthesis and antiproliferative activity of 6,7-aryl/hetaryl coumarins

Two different series of novel analogs of 6,7-aryl/hetaryl coumarins 4a-4h and 8i-8l have been synthesized by using Suzuki-Miyara cross coupling reaction from 4-methyl-2-oxo-2H-chromen-7-yl trifluoro-methanesulfonate and 4-methyl-2-oxo-2H-chromen-6-yl trifluoromethanesulfonate in high yields (70-90%). All synthesized compounds were elucidated by means of IR, 1H NMR, 13C NMR, and MS spectra. The synthesized compounds were tested for antiproliferative activity against different human cancer cell lines (SiHa, MDAMB-231, and PANC-1) and some of products demonstrated the distinctive effect.

Novel thiazoline-coumarin hybrid compounds containing sugar moieties: synthesis, biological evaluation and molecular docking study as antiproliferative agents

A new series of 2,3-thiazoline-coumarin hybrid compounds that containedd-glucose andd-galactose moieties (4a-g) were synthesized and their cytotoxic activity was evaluated against breast adenocarcinoma (MCF-7), human liver cancer (HepG2), human cervical cancer (HeLa), human melanoma cancer (SK-Mel-2), and human lung cancer (LU-1) cells. To reveal their selectivity toward cancer cells, the compounds were also tested against the human fibroblast cell line MRC-5. The synthesized compounds exhibited potent cytotoxic activity against the tested cell lines with IC50values of 1.18-11.32, 1.91-9.81, 1.96-13.16, 1.35-16.12, and 2.12-15.92 μM (against MCF-7, HepG2, HeLa, SK-Mel-2, and LU-1 cells, respectively) compared with Sorafenib, doxorubicin, and 5-fluorouracil. Interestingly, compounds4a-gdisplayed selectivity toward cancer cell lines over MRC-5 (IC503.97-25.75 μM). The most active compounds, including4d,4e, and4f, also displayed potent inhibitory activity against EGFR and HER2 kinases (IC500.15-0.31 and 0.15-0.25 μM, respectively) compared with the standard drug Sorafenib (IC50= 0.11 and 0.13 μM, respectively). Molecular docking also showed that the hydrogen binding interactions often occurred between the CO lactone of the coumarin ring and appropriate amino acid residues, which played a key role in enhancing its potency against both enzymes.

A Reusable Column Method Using Glycopolymer-Functionalized Resins for Capture–Detection of Proteins and Escherichia coli

The use of glycopolymer-functionalized resins (Resin–Glc), as a solid support, in?column mode for bacterial/protein capture and quantification is explored. The Resin–Glc is synthesized?from commercially available chloromethylated polystyrene?resin and glycopolymer, and is characterized by fourier transform infrared spectroscopy, thermogravimetry, and elemental analysis. The percentage of glycopolymer functionalized on Resin–Glc is accounted to be 5 wt%. The ability of Resin–Glc to selectively capture lectin, Concanavalin A, over Peanut Agglutinin, reversibly, is demonstrated for six cycles of experiments. The bacterial sequestration study using SYBR (Synergy Brands, Inc.) Green I tagged?Escherichia coli/Staphylococcus aureus?reveals the ability of Resin–Glc to selectively capture?E. coli?over?S. aureus. The quantification of captured cells in the column is carried out by enzymatic colorimetric assay using methylumbelliferyl glucuronide?as the substrate. The?E. coli?capture studies reveal a consistent capture efficiency of 105?CFU (Colony Forming Units) g?1 over six cycles. Studies with spiked tap water samples show satisfactory results for?E. coli?cell densities ranging from 102 to 107?CFU mL?1. The method portrayed can serve as a basis for the development of a reusable solid support in capture and detection of proteins and bacteria.

Recyclable cellulose nanocrystal supported Palladium nanoparticles as an efficient heterogeneous catalyst for the solvent-free synthesis of coumarin derivatives via von Pechmann condensation

2-Amino pyrimidine nanocellulose-supported Palladium nanoparticles (CNC-AMPD-Pd) as a novel bio supported nanocatalyst was prepared and characterized by ICP-AES, FT-IR, XRD, SEM, TEM, TGA and EDX techniques. The nanocatalyst demonstrated outstanding performance in Pechmann condensation between different substituted phenols and ethyl acetoacetate to obtain coumarin derivatives in good to excellent yields. The catalyst is easily recycled and reused without loss of the catalytic activity. The combined merits of reusable catalyst and solvent-free reaction conditions make the condensation with safe operation, no leaching of pd into environment, low pollution, rapid access to products and simple workup.

Cu (I) Catalyzed One Pot SN-Click Reactions of Halogenated Coumarins and 1-aza-coumarins

A one pot three component, copper catalyzed azide-alkyne cycloaddition reaction has been employed for the synthesis of bis-coumarinyl triazoles (A–D) using 4-chloro, 4-bromomethyl, 3-bromoacetyl and 4-bromomethyl-1-aza-coumarins (I–IV), sodium azide, and coumarin propargyl ethers (V–IX) in moderate yields.

A green and convenient approach for the one-pot solvent-free synthesis of coumarins and β-amino carbonyl compounds using Lewis acid grafted sulfonated carbon@titania composite

Abstract: This paper reports an efficient protocol for the synthesis of coumarins via Pechmann reaction, and β-amino carbonyl compounds via aza-Michael reaction using catalytic amount of solid Lewis acid catalyst, C@TiO2–SO3–SbCl2. Six different catalysts were prepared by covalent immobilization of homogeneous Lewis acids onto sulfonated carbon@titania composite derived from amorphous carbon and nano-titania. Among various catalysts tested, C@TiO2–SO3–SbCl2 showed superior catalytic activity. The catalyst could be recycled without significant loss of its catalytic activity and demonstrated versatile catalysis for a wide range of substrates. Graphical abstract: [Figure not available: see fulltext.]