66185-72-6

Basic information

• Product Name: 2H-1-Benzopyran-2-one, 7-(benzoyloxy)-4-methyl-
• CAS NO: 66185-72-6
• Molecular Formula: C17H12O4
• Molecular Weight: 280.28
• Mol File: 66185-72-6.mol

Chemical Properties

• CAS DataBase Reference: 2H-1-Benzopyran-2-one, 7-(benzoyloxy)-4-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-1-Benzopyran-2-one, 7-(benzoyloxy)-4-methyl-(66185-72-6)
• EPA Substance Registry System: 2H-1-Benzopyran-2-one, 7-(benzoyloxy)-4-methyl-(66185-72-6)

Safety Data

• Hazardous Substances Data: 66185-72-6(Hazardous Substances Data)

Upstream product

• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 98-88-4 benzoyl chloride 
• 93-97-0 benzoic acid anhydride 
• 108-46-3 recorcinol 
• 65-85-0 benzoic acid 

Downstream Products

• 20312-83-8 8-Benzoyl-7-hydroxy-4-methylcoumarin 
• 2555-29-5 8-acetyl-7-hydroxy-4-methyl-2H-chromen-2-one 
• 1140-14-3 2,4-Dimethyl benzophenone 
• 68454-14-8 8-benzoyloxy-7-hydroxy-4-methylcoumarin 
• 67839-94-5 4-methyl-7-hydroxy-6-benzoylchromen-2-one 
• 86882-62-4 8-benzoyl-4-methyl-9-phenyl-2H-furo[2,3-h]chropmen-2-one 
• 424807-26-1 (8-benzoyl-4-methyl-2-oxo-2H-chromen-7-yloxy)-acetic acid ethyl ester 
• 113765-91-6 (8-benzoyl-4-methyl-2-oxo-2H-chromen-7-yloxy)-acetic acid 
• 113765-92-7 4-methyl-9-phenylfuro[2,3-h]chromen-2-one 
• 25855-75-8 (2,6-dimethoxyphenyl)(phenyl)methanone 
• 63411-81-4 benzoyl-resorcinol 
• 245728-25-0 8-Benzoyl-7-hydroxy-4-methylcoumarin oxime 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 6748-68-1 8-acetyl-7-hydroxycoumarin 

Relevant articles and documents

Tris(pentafluorophenyl)borane catalyzed acylation of alcohols, phenols, amines, and thiophenols under solvent-free condition

The acylation of alcohols, phenols, amines, and thiophenols was accomplished with 0.5 mol % of tris(pentafluorophenyl)borane [B(C 6F5)3] at ambient temperature under solvent-free condition. Major advantages of this method include high yield, short reaction time, simple procedure, compatibility with sensitive protecting groups as well as other functional groups, absence of racemization of optical active compounds, and epimerization of sugars.

Semisynthesis, ex vivo evaluation, and SAR studies of coumarin derivatives as potential antiasthmatic drugs

Asthma is a chronic inflammatory disorder that causes contraction in the smooth muscle of the airway and blocking of airflow. Reversal the contractile process is a strategy for the search of new drugs that could be used for the treatment of asthma. This work reports the semisynthesis, ex vivo relaxing evaluation and SAR studies of a series of 18 coumarins. The results pointed that the ether derivatives 1-3, 7-9 and 13-15 showed the best activity (E max = 100%), where compound 2 (42 μM) was the most potent, being 4-times more active than theophylline (positive control). The ether homologation (methyl, ethyl and propyl) in position 7 or positions 6 and 7 of coumarins lead to relaxing effect, meanwhile formation of esters generated less active compounds than ethers. The SAR analysis showed that it is necessary the presence of two small ether groups and the methyl group at position 4 (site 3) encourage biological activity through soft hydrophobic changes in the molecule, without drastically affecting the cLogP.

Synthesis, spectral characterization and α-chymotrypsin activity of 7-O-substituted derivatives of 7-hydroxy-4-methyl-1-benzopyran-2-one

In this work, a series of O-alkyl/arenyl/acyl substituted derivatives of 7-hydorxy-4-methyl-1-benzenpyran-2-one (3a-l) was synthesized. The parent compound 7-hydroxy-4-methyl-1-benzenpyran-2-one (1) was geared up by the coupling of resorcinol (a) with ethylacetoacetate (b) in the presence of conc. sulphuric acid. Further, O-substituted derivatives of parent compound were prepared by treating with different electrophiles (2a-l) using sodium hydride as base and DMF as a solvent. The structure of these synthesized compounds were characterized by IR, EI-MS and 1H NMR. These derivatives were also screened against α-chymotrypsin enzyme to check their enzyme inhibition activity. All the compounds displayed a-chymotrypsin activity to varying degree.

Synthesis and evaluation of substituted 4-methyl-2-oxo-2H-chromen-7-yl phenyl carbamates as potent acetylcholinesterase inhibitors and anti-amnestic agents

The study aimed to synthesize and evaluate substituted 4-methyl-2-oxo-2H- chromen-7-yl phenylcarbamates as potent acetylcholinesterase (AChE) inhibitors and anti-amnestic agents. The compounds were evaluated for AChE and butyrylcholinesterase (BuChE) inhi

An efficient, mild and scalable synthesis of bioactive compounds containing the angelicin scaffold

An efficient, mild and scalable synthesis of angelicin scaffold based compounds was developed. Particularly, the new synthetic route described here circumvents the need for the previously reported key Fries rearrangement step, which uses impractically har

Anti-influenza drug discovery: Structure-activity relationship and mechanistic insight into novel angelicin derivatives

By using a cell-based high throughput screening campaign, a novel angelicin derivative 6a was identified to inhibit influenza A. (H1N1) virus induced cytopathic effect in Madin-Darby canine kidney cell culture in low micromolar range. Detailed structure-activity relationship studies of 6a revealed that the angelicin scaffold is essential for activity in pharmacophore B, while meta-substituted phenyl/2-thiophene rings are optimal in pharmacophore A and C. The optimized lead 4-methyl-9-phenyl-8-(thiophene-2-carbonyl)-furo[2,3-h] chromen-2-one (8g, IC50 = 70 nM) showed 64-fold enhanced activity compared to the high throughput screening (HTS) hit 6a. Also, 8g was found effective in case of influenza A (H3N2) and influenza B virus strains similar to approved anti-influenza drug zanamivir (4). Preliminary mechanistic studies suggest that these compounds act as anti-influenza agents by inhibiting ribonucleoprotein (RNP) complex associated activity and have the potential to be developed further, which could form the basis for developing additional defense against influenza pandemics.

COUMARIN COMPOUNDS AND THEIR USE FOR TREATING CANCER

Coumarin compounds of formula (I): wherein R1, R2, R3, R4, R5, R6, and X are defined herein. Also disclosed is a method for treating cancer with coumarin compounds.

Enzyme catalyzed acylation of 7-hydroxy-4methyl-2 H-chromenc-2-one using microwave

Acylation of pharmacologically important 7-hydroxy-4mcihyl-2 H-chromcnc-2-onc has been investigated in the presence of immobilized lipase under the influence of microwave. Commercially available lipase (Novozyme 435) under microwave leads to enhancement in rate of reaction in comparison with conventional heating in immobilized lipase catalyzed acylation with various acids. Different microwave assisted technologies were studied and compared. This paper investigates the synergism between enzyme catalysis and microwaves on acylation of 7hydroxy-4-mcthyl-2 H-chromcnc-2-onc, with different acids using lipase Novozyme 435.

COUMARIN COMPOUNDS AND THEIR USE FOR TREATING VIRAL INFECTION

A method for treating an infection with a virus. The method includes administering to a subject in need thereof an effective amount of one or more coumarin compounds of formula (I): wherein R1, R2, R3, R4, Rsub

A high-throughput, low-volume enzyme assay on solid support

A high-throughput enzyme assay is described that uses 1 μL or less of enzyme solution for each test Enzyme solutions are deposited by robotic handling in a throughput of over 1000 tests/h on the surface of silica gel plates that have been preimpregnated with fluorogenic substrates. The reaction is quantitated by fluorescence. The method is compatible with water-insoluble substrates (lipases), water-soluble substrates (glycosidases), whole-protein substrates (proteases), and enzyme inhibition measurements. Hydrolytically labile umbelliferyl esters can be used to assay lipases in this format without background hydrolysis. High throughput and reproducibility were tested by fingerprint analysis of lipases and esterases against 37 different fluorogenic ester substrates. A set of eight fluorogenic unbelliferyl esters was selected for optimal activity screening of lipases and esterases on silica gel plates.