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

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

Uses

Used in Pharmaceutical Industry:
4-HYDROXY-7-METHOXY-1H-QUINOLIN-2-ONE is used as a key intermediate in the synthesis of various pharmaceuticals for its biological activities. It contributes to the development of drugs targeting different therapeutic areas, such as anti-inflammatory, anti-cancer, and anti-infective agents, due to its ability to modulate biological pathways and interact with specific molecular targets.
Used in Agrochemical Industry:
In the agrochemical sector, 4-HYDROXY-7-METHOXY-1H-QUINOLIN-2-ONE serves as a crucial building block in the creation of pesticides and other crop protection agents. Its incorporation into these products enhances their effectiveness in controlling pests and diseases, thereby improving crop yields and quality.
Used in Organic Synthesis:
4-HYDROXY-7-METHOXY-1H-QUINOLIN-2-ONE is utilized as a versatile intermediate in organic synthesis for the production of a broad spectrum of compounds. Its unique structure allows for various chemical reactions, enabling the synthesis of complex molecules with potential applications in different industries, such as materials science, dyes, and fine chemicals.

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

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• 141-82-2 malonic acid 
• 52994-51-1 bis-2,4-dichlorophenyl malonate 
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• 50424-96-9 4-methoxy-2-nitro-benzoyl chloride 

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 
• 55934-21-9 2,4-dichloro-5-methoxyquinoline 
• 55934-22-0 2,4-dichloro-7-methoxyisoquinoline 
• 1309362-06-8 C₂₉H₂₈N₂O₇S 
• 1203608-18-7 ethyl 2-amino-4-(4-chlorophenyl)-5-hydroxy-8-methoxy-4H-pyrano[3,2-c]quinoline-3-carboxylate 
• 1203608-17-6 2-amino-4-(4-chlorophenyl)-5-hydroxy-8-methoxy-4H-pyrano[3,2-c]quinoline-3-carbonitrile 
• 74798-85-9 3-phenylaminomethylene-7-methoxyquinoline-2,4-dione 
• 102249-28-5 6-chloro-3-hydroxy-7-methoxy-3-(2,3,4-trimethoxyphenyl)-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 
• 102249-27-4 6-chloro-3-hydroxy-7-methoxy-3-(4-hydroxy-2-t-butylphenyl)-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 
• 102249-29-6 6-chloro-3-hydroxy-3-(4-hydroxyphenyl)-2,4-dioxo-1,2,3,4-tetrahydroquinoline 

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.

Hepatitis C virus inhibitors

Hepatitis C virus inhibitors having the general formula (I) are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

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.

Discovery and biological activity of 6BrCaQ as an inhibitor of the Hsp90 protein folding machinery

Heat shock protein90 (Hsp90) is a significant target in the development of rational cancer therapy, due to its role at the crossroads of multiple signaling pathways associated with cell proliferation and viability. Here, a novel series of Hsp90 inhibitors containing a quinolein-2-one scaffold was synthesized and evaluated in cell proliferation assays. Results from these structure-activity relationships studies enabled identification of the simplified 3-aminoquinolein-2-one analogue 2b (6BrCaQ), which manifests micromolar activity against a panel of cancer cell lines. The molecular signature of Hsp90 inhibition was assessed by depletion of standard known Hsp90 client proteins. Finally, processing and activation of caspases 7, 8, and 9, and the subsequent cleavage of PARP by 6BrCaQ, suggest stimulation of apoptosis through both extrinsic and intrinsic pathways. Hot stuff! A novel series of Hsp90 inhibitors containing a quinolein-2-one scaffold was synthesized and screened in cell proliferation assays. The most potent inhibitor, 6BrCaQ, exhibited strong antiproliferative activity against a panel of cancer cell lines and resulted in downregulation of Hsp90 client proteins. Moreover, 6BrCaQ induced a high level of apoptosis in MCF-7 breast cancer cells, and was found to mediate cell death in a p23-independent manner.

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.