15832-09-4

Basic information

• Product Name: 6-Methoxy-3(2H)-benzofuranone
• Synonyms: 6-Methoxy-3(2H)-benzofuranone;5-Fluoro-3-Benzofuranone;6-Methoxybenzofuran-3(2H)-one;6-Methoxy-3(2H)
• CAS NO: 15832-09-4
• Molecular Formula: C₉H₈O₃
• Molecular Weight: 164.15802
• Mol File: 15832-09-4.mol

Chemical Properties

• Melting Point: 119-120 °C(Solv: ethanol (64-17-5))
• Boiling Point: 313 °C at 760 mmHg
• Flash Point: 134.1 °C
• Appearance: /
• Density: 1.262 g/cm₃
• Vapor Pressure: 0.0114mmHg at 25°C
• Refractive Index: 1.557
• CAS DataBase Reference: 6-Methoxy-3(2H)-benzofuranone(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Methoxy-3(2H)-benzofuranone(15832-09-4)
• EPA Substance Registry System: 6-Methoxy-3(2H)-benzofuranone(15832-09-4)

Safety Data

• Hazardous Substances Data: 15832-09-4(Hazardous Substances Data)

Usage

Uses

Used in Flavoring and Fragrance Industry:
6-Methoxy-3(2H)-benzofuranone is used as a flavoring agent in food and beverages, adding a distinctive taste and aroma to a variety of products. It is also utilized as a fragrance in cosmetic and personal care products, providing a pleasant scent and enhancing the sensory experience of these items.
Used in Traditional Medicine:
In traditional medicine, 6-Methoxy-3(2H)-benzofuranone is employed for its antiseptic and analgesic properties, helping to treat minor injuries and alleviate pain.
Used in Pharmaceutical Industry:
6-Methoxy-3(2H)-benzofuranone is used as an antifungal, antibacterial, and antioxidant agent, contributing to the development of medications that combat infections and promote overall health.
Used in Research and Development:
Due to its potential applications, 6-Methoxy-3(2H)-benzofuranone is also used in research and development for exploring new uses and improving existing formulations in various industries.

InChI:InChI=1/C8H5FO2/c9-5-1-2-8-6(3-5)7(10)4-11-8/h1-3H,4H2

Upstream product

• 186581-53-3 diazomethane 
• 60-29-7 diethyl ether 
• 19202-27-8 2-acetoxy-4-methoxy-benzoyl chloride 
• 150-19-6 O-methylresorcine 
• 107-16-4 glycolonitrile 
• 78-97-7 2-hydroxy-propionitrile 
• 4940-44-7 2'-hydroxy-2,4'-dimethoxyacetophenone 
• 10035-10-6 hydrogen bromide 
• 52116-39-9 2-carboxymethoxy-4-methoxy-benzoic acid 
• 107-14-2 chloroacetonitrile 
• 415714-37-3 3-acetoxy-6-methoxy-benzofuran 
• 6272-26-0 6-hydroxybenzofuran-3-one 
• 77-78-1 dimethyl sulfate 
• 77336-36-8 1,3-dimethoxy-4-ethynylbenzene 

Downstream Products

• 94541-27-2 2-((Z)-2-hydroxy-4-methoxy-benzylidene)-6-methoxy-benzofuran-3-one 
• 93876-46-1 2-((Z)-2-hydroxy-4,6-dimethoxy-benzylidene)-6-methoxy-benzofuran-3-one 
• 4940-52-7 2-Benzylidene-6-methoxy-3(2H)-benzofuranone 
• 71005-54-4 (Z)-2-(2-hydroxybenzylidene)-6-methoxybenzofuran-3(2H)-one 
• 32396-82-0 6-methoxy-2-((Z)-vanillylidene)-benzofuran-3-one 
• 36685-46-8 (Z)-2-(3,4-dimethoxybenzylidene)-6-methoxybenzofuran-3(2H)-one 
• 32396-78-4 (Z)-2-(3,4-dihydroxybenzylidene)-6-methoxybenzofuran-3(2H)-one 
• 32396-77-3 (Z)-2-(2,4-dihydroxybenzylidene)-6-methoxybenzofuran-3(2H)-one 
• 132835-41-7 6-methoxy-2,2-diphenylbenzofuran-3(2H)-one 
• 108197-50-8 2-(p-methylbenzylidene)-6-methoxycoumaran-3-one 
• 108197-52-0 2-(p-nitrobenzylidene)-6-methoxycoumaran-3-one 
• 132835-40-6 6-methoxy-2-(2,4,6-trimethoxyphenyl)benzofuran-3(2H)-one 
• 108197-53-1 2-(o-methoxybenzylidene)-6-methoxycoumaran-3-one 
• 108197-51-9 2-(p-bromobenzylidene)-6-methoxycoumaran-3-one 

Relevant articles and documents

Synthesis of novel pyrazole derivatives and their tumor cell growth inhibitory activity

To find novel antitumor agents, a series of 1H-benzofuro[3,2-c]pyrazole derivatives 4a-e were designed and synthesized. The treatment of 6-methoxybenzofuran-3(2H)-one 3 with LiHMDS in anhydrous tetrahydrofuran (THF) followed by reaction with 3-substitued phenyl isothiocyanate gave the thioamide intermediates, which underwent condensation with hydrazine monohydrate in dioxane/EtOH (1:1) to provide the benzofuropyrazole derivatives 4a–e as well as the unexpected pyrazole derivatives 5a–e. In tumor cell growth inhibitory assay, all the benzofuropyrazole derivatives were not active against the breast tumor MCF-7 cell, only 4a was highly active and more potent than ABT-751 against the leukemia K562 (GI50 = 0.26 μM) and lung tumor A549 cells (GI50 = 0.19 μM), while other benzofuropyrazoles showed very weak inhibitory activity. In contrast, the pyrazoles 5a-e were in general more potent than the benzofuropyrazoles 4a–e. Compound 5a exhibited a similar tendency to that of 4a with high potency against K562 and A549 cells but weak effects on MCF-7 cell. Both pyrazoles 5b and 5e exhibited high inhibitory activities against K562, MCF-7 and A549 cells. The most active compound 5b was much more potent than ABT-751 against K562 and A549 cells with GI50 values of 0.021 and 0.69 M, respectively. Moreover, 5b was identified as a novel tubulin polymerization inhibitor with an IC50 of 7.30 M.

Total synthesis of (?)-4-desacetoxy-1-oxovindoline: Single atom exchange of an embedded core heteroatom in vindoline

A concise total synthesis of (?)-4-desacetoxy-1-oxovindoline is disclosed, bearing a single heteroatom exchange in the core structure of the natural product 4-desacetoxyvindoline. Central to the synthesis is powerful oxadiazole intramolecular [4 + 2]/[3 +

Discovery of the first-in-class dual PPARδ/γ partial agonist for the treatment of metabolic syndrome

The peroxisome proliferator-activated receptors (PPARs) exert vital function in the regulation of energy metabolism, which were considered as promising targets of metabolic syndrome. Until now, PPARδ/γ dual agonist is rarely reported, and thereby the pharmacologic action of PPARδ/γ dual agonist is still unclear. In this study, we identified a dual PPARδ/γ partial agonist 6 (ZLY06) based on the cyclization strategy of PPARα/δ dual agonist GFT505. ZLY06 revealed excellent pharmacokinetic profiles suitable for oral medication. Moreover, ZLY06 markedly improved glucolipid metabolism without weight gain, and alleviated fatty liver by promoting the β-oxidation of fatty acid and inhibiting hepatic lipogenesis. In contrast, weight gain and hepatic steatosis were observed in Rosiglitazone, a widely used PPARγ full agonist. All of these results indicated that ZLY06 exhibits potential benefits on metabolic syndrome, while no adverse effects related to PPARγ full agonist.

A Palladium-Catalyzed Oxa-(4+4)-Cycloaddition Strategy towards Oxazocine Scaffolds

A Pd-catalyzed oxa-(4+4)-cycloaddition between 1-azadienes and (2-hydroxymethyl)allyl carbonates is described. Aurone-derived azadienes furnished polycyclic 1,5-oxazocines in good yields. Interestingly, linear azadienes have also been involved and yielded monocyclic heterocycles with complete regioselectivity. DFT calculations were carried out to gain insight on this observation.

Aurone derivatives as promising antibacterial agents against resistant Gram-positive pathogens

A set of variously substituted aurones was synthesized and evaluated against Methicillin-Resistant S. aureus (MRSA) and P. aeruginosa. Several analogues were found active against MRSA, but no effect was recorded against P. aeruginosa. Compounds 27, 30 and 33 showed low cytotoxicity, and were tested against a full range of bacterial (Gram-positive and Gram-negative) and fungal species, including resistant strains. These aurones displayed a selective inhibition of Gram-positive bacteria with excellent Therapeutic Index values, while showing no significant action on several Gram-negative strains, H. pylori and V. alginolyticus being the only susceptible strains among the Gram-negative bacteria tested. A permeabilization assay showed that the antibacterial activity of at least some of the aurones could be linked to alterations of the bacterial membrane. Overall, this study endorses the use of the aurone scaffold for the development of new potent and selective antibacterial agents.

Design and synthesis of novel senkyunolide analogues as neuroprotective agents

A class of senkyunolide analogues bearing benzofuranone fragment were designed, synthesized and evaluated for their neuroprotective effect in models of oxygen glucose deprivation (OGD) and oxidative stress. All tested compounds showed neuroprotection profile based on the cell viability assay. In particular, derivatives 1f–1i possessing furoxan-based nitric oxide releasing functionality exhibited significant biological activities in OGD models. More importantly, compound 1g containing short linker with furoxan displayed the most potent neuroprotection at the concentration of 100 μM (cell survival up to 145.2%). Besides, 1g also showed the middle level neuroprotective effect in model of oxidative stress.

Benzofuranone derivatives as well as preparation method and application thereof

The invention discloses benzofuranone derivatives as well as a preparation method and medical application thereof, and provides the benzofuranone derivatives, the preparation method thereof and an application of pharmaceutical composition containing the d

Synthesis of 6-hydroxyaurone analogues and evaluation of their α-glucosidase inhibitory and glucose consumption-promoting activity: Development of highly active 5,6-disubstituted derivatives

A series of 6-hydroxyaurones and their analogues have been synthesized and evaluated for their in vitro α-glucosidase inhibitory and glucose consumption-promoting activity. These compounds exhibited varying degrees of α-glucosidase inhibitory activity, 11 of them showing higher potency than that of the control standard acarbose (IC50?=?50.30?μM). Surprisingly, analogues devoid of a substituent at C-2 but having an aryl group at C-5 were found to be highly active (e.g., 7f, IC50?=?9.88?μM). Docking analysis substantiated these findings. The kinetic analysis of compound 7f, the most potent α-glucosidase inhibitor of this study, revealed that it inhibited α-glucosidase in an irreversible and mixed competitive mode. In addition, compounds 7f and 10c exhibited significant glucose consumption promoting activity at 1?μM.

Discovery of benzofuran-3(2H)-one derivatives as novel DRAK2 inhibitors that protect islet β-cells from apoptosis

Death-associated protein kinase-related apoptosis-inducing kinase-2 (DRAK2) is a serine/threonine kinase that plays a key role in a wide variety of cell death signaling pathways. Inhibition of DRAK2 was found to efficiently protect islet β-cells from apoptosis and hence DRAK2 inhibitors represent a promising therapeutic strategy for the treatment of diabetes. Only very few chemical entities targeting DRAK2 are currently known. We carried out a high throughput screening and identified compound 4 as a moderate DRAK2 inhibitor with an IC50value of 3.15?μM. Subsequent SAR studies of hit compound 4 led to the development of novel benzofuran-3(2H)-one series of DRAK2 inhibitors with improved potency and favorable selectivity profiles against 26 selected kinases. Importantly, most potent compounds 40 (IC50?=?0.33?μM) and 41 (IC50?=?0.25?μM) were found to protect islet β-cells from apoptosis in dose-dependent manners. These data support the notion that small molecule inhibitors of DRAK2 represents a promising strategy for the treatment of diabetes.

Carboxylated aurone derivatives as potent inhibitors of xanthine oxidase

Xanthine oxidase is a potential target for treatment of hyperuricemia and gout. In this study, a number of A- and B-ring carboxylated aurone derivatives were synthesized and evaluated for their ability to inhibit xanthine oxidase in vitro. According to the results obtained, two different ranges of inhibitory activity were observed. The aurones with carboxylic acid group at the 4′-position of B-ring were found to be potent inhibitors of the enzyme with IC50 values in the low micromolar range. The effects of these compounds were about 50 fold higher than of A-ring modified aurones with carboxymethoxy group at the 6-position. The binding modes of the carboxylated aurones in the active site of xanthine oxidase were explained using molecular docking calculations.