27037-34-9

Basic information

• Product Name: 4-HYDROXY-7-METHOXY-1H-QUINOLIN-2-ONE
• Synonyms: AURORA KA-2384;4-HYDROXY-7-METHOXY-1H-QUINOLIN-2-ONE;4-Hydroxy-7-methoxy-2H-quinolin-2-one;2,4-Dihydroxy-7-methoxyquinoline;4-hydroxy-7-Methoxyquinolin-2(1H)-one;4-hydroxy-7-methoxy-2-oxo-1,2-dihydroquinoline
• CAS NO: 27037-34-9
• Molecular Formula: C₁₀H₉NO₃
• Molecular Weight: 191.18
• Mol File: 27037-34-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 339-340 °C
• Boiling Point: 356.7ºC at 760 mmHg
• Flash Point: 169.5ºC
• Appearance: /
• Density: 1.355g/cm3
• Vapor Pressure: 1.05E-05mmHg at 25°C
• Refractive Index: 1.623
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: 4-HYDROXY-7-METHOXY-1H-QUINOLIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-7-METHOXY-1H-QUINOLIN-2-ONE(27037-34-9)
• EPA Substance Registry System: 4-HYDROXY-7-METHOXY-1H-QUINOLIN-2-ONE(27037-34-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 27037-34-9(Hazardous Substances Data)

Usage

General Description

4-HYDROXY-7-METHOXY-1H-QUINOLIN-2-ONE, also known as quinolin-2-one, is a chemical compound with the molecular formula C10H9NO3. It is a derivative of quinolinone, which is a heterocyclic compound with a bicyclic structure containing a quinoline and a ketone. The compound has a hydroxyl group and a methoxy group attached to the quinoline ring. Quinolin-2-one has various biological activities and is used in the synthesis of pharmaceuticals and agrochemicals. Its structure and properties make it a valuable intermediate in organic synthesis, as it can be used in the production of a wide range of compounds with diverse applications.

InChI:InChI=1/C10H9NO3/c1-14-6-2-3-7-8(4-6)11-10(13)5-9(7)12/h2-5H,1H3,(H2,11,12,13)

Upstream product

• 50424-96-9 4-methoxy-2-nitro-benzoyl chloride 
• 105-53-3 diethyl malonate 
• 15116-23-1 N,N'-bis(3-methoxyphenyl)malonamide 
• 141-82-2 malonic acid 
• 536-90-3 m-Anisidine 
• 52994-51-1 bis-2,4-dichlorophenyl malonate 

Downstream Products

• 100192-50-5 4,7-dimethoxy-1-methyl-1H-quinolin-2-one 
• 102249-21-8 7-methoxy-3,3,6-trichloro-2,4-dioxo-1,2,3,4-tetrahydroquinoline 
• 102249-22-9 7-methoxy-3,3,6,8-tetrachloro-2,4-dioxo-1,2,3,4-tetrahydroquinoline 
• 74798-85-9 3-phenylaminomethylene-7-methoxyquinoline-2,4-dione 
• 405296-92-6 2-amino-8-methoxy-5-oxo-4-phenyl-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carbonitrile 
• 920276-14-8 cyclohexane-1,3-dione mono-(7-methoxy-2-oxo-1,2-dihydroquinolin-4-yl)hydrazone 
• 102249-29-6 6-chloro-3-hydroxy-3-(4-hydroxyphenyl)-2,4-dioxo-1,2,3,4-tetrahydroquinoline 
• 102249-30-9 6-chloro-3-hydroxy-3-(2,4-dihydroxyphenyl)-7-methoxy-2,4-dioxo-1,2,3,4-tetrahydroquinoline 
• 102249-27-4 6-chloro-3-hydroxy-7-methoxy-3-(4-hydroxy-2-t-butylphenyl)-2,4-dioxo-1,2,3,4-tetrahydroquinoline 
• 102249-26-3 6-chloro-3-hydroxy-7-methoxy-3-(2-hydroxy-5-methyl-3-t-butylphenyl)-2,4-dioxo-1,2,3,4-tetrahydroquinoline 
• 102249-28-5 6-chloro-3-hydroxy-7-methoxy-3-(2,3,4-trimethoxyphenyl)-2,4-dioxo-1,2,3,4-tetrahydroquinoline 
• 55934-22-0 2,4-dichloro-7-methoxyisoquinoline 
• 1203608-17-6 2-amino-4-(4-chlorophenyl)-5-hydroxy-8-methoxy-4H-pyrano[3,2-c]quinoline-3-carbonitrile 
• 1203608-18-7 ethyl 2-amino-4-(4-chlorophenyl)-5-hydroxy-8-methoxy-4H-pyrano[3,2-c]quinoline-3-carboxylate 

Relevant articles and documents

Syntheses and fluorescent properties of 6-methoxy-2-oxoquinoline-3,4- dicarbonitriles and 6,7-dimethoxy-2-oxoquinoline-3,4-dicarbonitriles

4-Chlorocarbostyrils 3, 12, 17, 24, 26 with methoxy substituents in 6, 7, or 6,7-position react with potassium cyanide in a p-toluenesulfinate mediated reaction either to the highly fluorescent and stable 2-oxoquinoline-3,4- dicarbonitriles 6, 27, 29, 30 or at slightly lower temperatures to 4-monocarbonitriles 5, 13, 18. 4-Chlorocarbostyril 3 and lithium p-toluenesulfinate gave pure 4-toluenesulfonylquinolone 4, which reacted with potassium cyanide either to monocarbonitrile 5 or dicarbonitrile 6, depending on the reaction conditions. 4-Trifluoromethylquinolones 9 and 19 were prepared for fluorescence comparison from the appropriate methoxyaniline and 4,4,4-trifluoroacetoacetate. The fluorescence properties such as emission wavelengths and quantum yields of 6-methoxyderivatives 4, 5, 6, 9, 13 were studied and compared with those of 7-methoxy derivatives 18, 19 and 6,7-dimethoxyderivatives 27, 28, 29, 30. 6,7-Dimethoxy derivatives show best results, showing long-waved fluorescence spectra up to 520 nm and acceptable quantum yields up to 0.46 for 3,4-dicyano derivative 27 excited at 440 nm in acetonitrile.

Synthesis and SAR studies of novel 6,7,8-substituted 4-substituted benzyloxyquinolin-2(1H)-one derivatives for anticancer activity

Background and Purpose 4-Phenylquinolin-2(1H)-one (4-PQ) derivatives can induce cancer cell apoptosis. Additional new 4-PQ analogs were investigated as more effective, less toxic antitumour agents. Experimental Approach Forty-five 6,7,8-substituted 4-substituted benzyloxyquinolin-2(1H)-one derivatives were synthesized. Antiproliferative activities were evaluated using a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazoliun bromide assay and structure-activity relationship correlations were established. Compounds 9b, 9c, 9e and 11e were also evaluated against the National Cancer Institute-60 human cancer cell line panel. Hoechst 33258 and Annexin V-FITC/PI staining assays were used to detect apoptosis, while inhibition of microtubule polymerization was assayed by fluorescence microscopy. Effects on the cell cycle were assessed by flow cytometry and on apoptosis-related proteins (active caspase-3, -8 and -9, procaspase-3, -8, -9, PARP, Bid, Bcl-xL and Bcl-2) by Western blotting. Key Results Nine 6,7,8-substituted 4-substituted benzyloxyquinolin-2(1H)-one derivatives (7e, 8e, 9b, 9c, 9e, 10c, 10e, 11c and 11e) displayed high potency against HL-60, Hep3B, H460, and COLO 205 cancer cells (IC50 50 > 50 μM). Particularly, compound 11e exhibited nanomolar potency against COLO 205 cancer cells. Mechanistic studies indicated that compound 11e disrupted microtubule assembly and induced G2/M arrest, polyploidy and apoptosis via the intrinsic and extrinsic signalling pathways. Activation of JNK could play a role in TRAIL-induced COLO 205 apoptosis. Conclusion and Implications New quinolone derivatives were identified as potential pro-apoptotic agents. Compound 11e could be a promising lead compound for future antitumour agent development.

A CONVENIENT APPROACH TO THE SYNTHESIS OF PRENYL-, FURO- AND PYRANO-QUINOLINE ALKALOIDS OF THE RUTACEAE

A convenient method for the synthesis of 4-hydroxy-3-prenyl-2-quinolones, wjich have been recognised as precursors to prenyl-, furo- and pyranoquinoline alkaloids of the Rutaceae is described.The methodology involves C,C-diprenylation of 2,4-dihydroxyquinoline followed by partial deallylation using sodium hydrogen telluride reagent.