18706-63-3

Basic information

• Product Name: 4-Hydroxy-6-Methyl-2H-Pyrano[3,2-c]Quinoline-2,5(6H)-Dione
• Synonyms: 2H-Pyrano[3,2-c]quinoline-2,5(6H)-dione;4-hydroxy-6-methyl-;4-Hydroxy-6-methyl-6H-pyrano[3,2-c]quinoline-2,5-dione
• CAS NO: 18706-63-3
• Molecular Formula: C₁₃H₉NO₄
• Molecular Weight: 0
• Mol File: 18706-63-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 327-328 °C(Solv: acetic acid (64-19-7))
• Boiling Point: 467.3°Cat760mmHg
• Flash Point: 236.4°C
• Appearance: /
• Density: 1.54g/cm³
• Vapor Pressure: 1.55E-09mmHg at 25°C
• Refractive Index: 1.71
• PKA: 11.40±0.20(Predicted)
• CAS DataBase Reference: 4-Hydroxy-6-Methyl-2H-Pyrano[3,2-c]Quinoline-2,5(6H)-Dione(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxy-6-Methyl-2H-Pyrano[3,2-c]Quinoline-2,5(6H)-Dione(18706-63-3)
• EPA Substance Registry System: 4-Hydroxy-6-Methyl-2H-Pyrano[3,2-c]Quinoline-2,5(6H)-Dione(18706-63-3)

Safety Data

• Hazardous Substances Data: 18706-63-3(Hazardous Substances Data)

Usage

General Description

4-Hydroxy-6-Methyl-2H-Pyrano[3,2-c]Quinoline-2,5(6H)-Dione is a chemical compound that belongs to the pyranoquinoline group. It is a heterocyclic molecule with a quinoline core and a pyran ring attached to it. The compound contains a hydroxyl group and a methyl group, and it is known for its antioxidant and cytotoxic properties. It has been studied for its potential use in cancer treatment and as an antibacterial agent. The compound's structure and properties make it a promising candidate for further research and development in the field of pharmaceuticals and medicinal chemistry.

InChI:InChI=1/C13H9NO4/c1-14-8-5-3-2-4-7(8)12-11(13(14)17)9(15)6-10(16)18-12/h2-6,16H,1H3

Upstream product

• 100-61-8 N-methylaniline 
• 105-53-3 diethyl malonate 

Downstream Products

• 54289-76-8 3-acetyl-4-hydroxy-1-methyl-2(1H)-quinolone 
• 1410922-08-5 1-methyl-4-hydroxy3-(8-(4-chlorophenyl)-6-oxo-6H-7,9-dicarbonitrilepyrido[1,2-b][1,2,4]triazin-2-yl)quinolin-2(1H)-one 
• 127855-77-0 3-acetyl-1-methyl-4-<(triphenylphosphoranylidene)amino>-2(1H)-quinolone 
• 127855-74-7 3-acetyl-1-methyl-4-tolylsulfonyl-2(1H)-quinolone 
• 127855-79-2 3-acetyl-4-benzylamino-1-methyl-2(1H)-quinolone 
• 71833-97-1 3-(N-benzylethanimidoyl)-4-hydroxy-1-methyl-2(1H)-quinolinone 
• 95855-01-9 (4-Acetoxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl) (5-Methyl-1,3,4-oxadiazol-2-yl) Ketone 
• 219479-27-3 (4-Hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl) (Tetrazol-5-yl) Ketone 
• 1677-46-9 4-hydroxy-1-methyl-2(1H)-quinolone 
• 128405-30-1 2-Amino-6-(4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl)-4-(4-methoxy-phenyl)-4H-pyran-3-carboxylic acid ethyl ester 
• 128405-29-8 2-Amino-6-(4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl)-4-phenyl-4H-pyran-3-carboxylic acid ethyl ester 
• 128405-31-2 2-Amino-4-(4-chloro-phenyl)-6-(4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl)-4H-pyran-3-carboxylic acid ethyl ester 
• 128405-28-7 2-Amino-4-(4-chloro-phenyl)-6-(4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl)-4H-pyran-3-carbonitrile 
• 128405-26-5 2-Amino-6-(4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl)-4-phenyl-4H-pyran-3-carbonitrile 

Relevant articles and documents

Synthesis, cytotoxic activity, ADMET and molecular docking study of quinoline-based hybrid compounds of 1,5-benzothiazepines

Some α,β-unsaturated ketones 4a-g of 3-acetyl-4-hydroxyquinolin-2(1H)-one were prepared by its reaction with (hetero)aromatic aldehydes with yields of 61-87% using piperidine as a catalyst. These ketones reacted with o-aminothiophenol in the presence of acetic acid to afford a series of new hybrid compounds, quinoline-benzothiazepine, 6a-g. The yields of benzothiazepines 6a-g were 62-85%. All the synthesized compounds 6a-g were screened for their in vitro anticancer activity against human hepatocellular carcinoma HepG2 and squamous cell carcinoma KB cancer lines. Compounds 6d and 6g had the best activity in the series, with IC50 values of 0.25 and 0.27 μg mL-1, respectively, against HepG2, and of 0.26 and 0.28 μM, respectively, against KB cell lines. ADMET properties showed that compounds 6c and 6g possessed drug-likeness behavior. Cross-docking results indicated that residues GLN778(A), DA12(F), and DG13(F) in the binding pocket were potential ligand binding hot-spot residues for compounds 6c and 6g. This journal is

Rapid preparation of pyranoquinolines using microwave dielectric heating in combination with fractional product distillation

4-Hydroxy-6-methyl-2H-pyrano[3,2-c]quinoline-2,5(6H)-dione was prepared by microwave-assisted cyclocondensation of N-methylaniline with 2 equiv of diethyl malonate. Key to the success of the synthesis was the use of open vessel controlled microwave heating technology, allowing the simultaneous removal of the formed ethanol from the reaction mixture by fractional distillation.

Transcription factor modulating compounds and methods of use thereof

Substituted benzoimidazole compounds useful as anti-infectives that decrease resistance, virulence, or growth of microbes are provided. Methods of making and using substituted benzoimidazole compounds, as well as pharmaceutical preparations thereof, in, e.g., reducing antibiotic resistance and inhibiting biofilms.