70254-43-2

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Quinolinediol is used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and agricultural products.
Used in Cancer Treatment:
2,4-Quinolinediol is studied for its potential applications in the treatment of cancer, with further research needed to understand its full potential benefits and drawbacks in this area.
Used as an Antioxidant:
2,4-Quinolinediol has been studied for its antioxidant properties, which could be utilized in various applications to prevent oxidative damage and promote overall health.
Used in Antimicrobial Agents Development:
2,4-Quinolinediol has been found to exhibit antimicrobial properties and is being investigated for its potential use in the development of new antimicrobial agents, with further research required to fully understand its potential benefits and drawbacks in this area.

InChI:InChI=1/C9H7NO2/c11-8-5-9(12)10-7-4-2-1-3-6(7)8/h1-5H,(H2,10,11,12)

Upstream product

• 91-22-5 quinoline 
• 20628-20-0 ethyl N-acetylanthranilate 
• 15580-32-2 malonanilic acid 
• 22751-16-2 2-nitrobenzoylacetic acid 
• 141-82-2 malonic acid 
• 62-53-3 aniline 
• 134-20-3 2-carbomethoxyaniline 
• 89-52-1 o-acetylamino-benzoic acid 
• 621-10-3 N,N'-diphenylmalonamide 
• 120450-95-5 4-ethoxycarbonyloxyquinolin-2(1H)-one 
• 42997-26-2 4-allyloxy-2-quinolone 
• 189274-62-2 Oxazolo[3,2-a]quinoline-1,2,5-trione 
• 408508-16-7 (2-formylamino-phenyl)-propiolic acid ethyl ester 
• 75-44-5 phosgene 

Downstream Products

• 62668-79-5 3-benzyl-4-hydroxy-6H-pyrano[3,2-c]quinoline-2,5-dione 
• 62668-78-4 4-hydroxy-3-phenyl-6H-pyrano[3,2-c]quinoline-2,5-dione 
• 62668-76-2 4-hydroxy-3-phenyl-10H-pyrano[2,3-b]quinoline-2,5-dione 
• 62668-77-3 3-benzyl-4-hydroxy-10H-pyrano[2,3-b]quinoline-2,5-dione 
• 88893-96-3 2-methyl-3-phenyl-5H-furo[3,2-c]quinolin-4-one 
• 142071-45-2 N-(5,6-dihydro-2,5-dioxo-2H-pyrano<3,2-c>quinoline-3-yl)benzamide 
• 104654-88-8 2,3-Dihydro-3,3-dimethyl-2-methylenefuro<3,2-c>quinolin-4-one 
• 523-64-8 flindersine 
• 112547-34-9 1,1-dimethyl-2-methylen-2,3-dihydrooxazolo<3,2-a>chinolin-5-on 
• 21873-59-6 3,3-bis(γ,γ-dimethylallyl)-2.4-dioxo-1,2,3,4-tetrahydroquinoline 
• 6431-84-1 4-hydroxy-3-(3-methylbut-2-enyl) quinolin-2(1H)one 
• 18118-29-1 4-(3',3'-Dimethylallyloxy)-3-(3'',3''-dimethylallyl)-2-chinolon 
• 54357-78-7 4-(3',3'-Dimethylallyloxy)-2-chinolon 
• 77587-21-4 4-(3,7-dimethylocta-2,6-dienyloxy)-2-quinolone 

Relevant academic research and scientific papers

Vibrational spectroscopic and molecular docking study of (2E)-N-(4-chloro-2-oxo-1,2-dihydroquinolin-3-yl)-3-phenylprop-2-enamide

FT-IR and FT-Raman spectra of (2E)-N-(4-chloro-2-oxo-1,2-dihydroquinolin-3-yl)-3-phenylprop-2-enamide were recorded and analyzed experimentally and theoretically. The synthesis, 1H NMR and PES scan results are also discussed. Nonlinear optical behavior of the examined molecule was investigated by the determination of first hyperpolarizability. The calculated HOMO and LUMO energies show the chemical activity of the molecule. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using NBO analysis. From the MEP it is evident that the negative charge covers the carbonyl group and the positive region is over the NH group. The calculated geometrical parameters (SDD) are in agreement with that of similar derivatives. Molecular docking simulations against targets from Mycobacterium tuberculosis are reported and the results suggest that the compound might exhibit inhibitory activity against PknB.

4-Hydroxy-2-quinolones. 97. Simple synthesis of the esters of 4-halo-substituted 2-oxo-1,2-dihydroquinoline-3-carboxylic acids

Short term treatment of 3-ethoxycarbonyl-4-morpholino-2-oxo-1,2- dihydroquinoline with aqueous solutions of hydrohalogen acids leads to the formation of the ethyl esters of 4-halo-substituted 2-oxo-1,2-dihydroquinoline- 3-carboxylic acids. Hydrolysis in HF is possible on extended boiling only to the 4-hydroxy derivative.

One-step Synthesis of 3-Unsubstituted 4-Hydroxy-2(1H)-Quinoline

3-Unsubstituted 4-hydroxy-2(1H)-quinolone (DHQ) derivatives were synthesized from aniline derivatives and diethyl malonate at low temperature using AlCl3 as catalyst and Eaton reagent as acidic environment. A reaction mechanism was proposed and elucidated. Different synthetic intermediates are specially prepared or purified and used to understand the reaction and validation mechanism.

Thiophene quinolone compound as well as preparation method and application thereof

The invention belongs to the field of medicines, and particularly relates to a thiophene quinolone compound as well as a preparation method and application thereof. The structural formula of the thiophene quinolone compound disclosed by the invention is shown I. The thiophene quinolone compound shown in the formula I is obtained, CDK5 inhibition activity is high, and water solubility is good.

Sequential Oxidative Fragmentation and Skeletal Rearrangement of Peroxides for the Synthesis of Quinazolinone Derivatives

For the first time, the sequential reaction of peroxyoxindole that involves base-promoted oxidative fragmentation to isocyanate formation and primary amine or amino alcohol accelerated skeletal rearrangement to synthesize exo-olefinic-substituted quinazolinone or oxazoloquinazolinone is reported. The advantages of this new reaction include a broad substrate scope and transition-metal-free and room-temperature conditions. The formation of the isocyanate as a key intermediate that accelerates oxidative skeletal rearrangement has been confirmed by trapping experiments and spectroscopic evidence.

Identification and molecular modeling of new quinolin-2-one thiosemicarbazide scaffold with antimicrobial urease inhibitory activity

Abstract: A new series of 6-substituted quinolin-2-one thiosemicarbazides 6a–j has been synthesized. The structure of the target compounds was proved by different spectroscopic and elemental analyses. All the designed final compounds were evaluated for their in vitro activity against the urease-producing R. mucilaginosa and Proteus mirabilis bacteria as fungal and bacterial pathogens, respectively. Moreover, all compounds were in vitro tested as potential urease inhibitors using the cup-plate diffusion method. Compounds 6a and 6b were the most active with (IC50 = 0.58 ± 0.15 and 0.43 ± 0.09?μM), respectively, in comparison with lead compound I (IC50 = 1.13 ± 0.00?μM). Also, the designed compounds were docked into urease proteins (ID: 3LA4 and ID: 4UBP) using Open Eye software to understand correctly about ligand–receptor interactions. The docking results revealed that the designed compounds can interact with the active site of the enzyme through multiple strong hydrogen bonds. Moreover, rapid overlay of chemical structures’ analysis was described to understand the 3D QSAR of synthesized compounds as urease inhibitors. The results emphasize the importance of polar thiosemicarbazide directly linked to 6-substituted quinolone moieties as promising antimicrobial urease inhibitors. Graphic abstract: [Figure not available: see fulltext.]

Method for preparing 4-hydroxyquinolin-2(1H)-one compound

The invention discloses a method for preparing a 4-hydroxyquinolin-2(1H)-one compound, which comprises the following steps of: reacting 2-ethynylaniline as shown in a formula (1) and carbon dioxide which are used as raw materials in an ionic liquid in the presence of a silver salt catalyst to obtain the 4-hydroxyquinoline-2 (1H)-one compound as shown in a formula (II). The reaction equation is shown in the specification. When the method disclosed by the invention is applied to the reaction for preparing the 4-hydroxyquinolin-2(1H)-one compound, the reaction conditions are relatively mild, the dosage of the silver salt catalyst is small, the separation and purification process of the product is relatively simple, the product yield is high, and the application range of a substrate is wide.

Preparation method of high-purity 4-hydroxy-quinoline-2 (1H)-ketone

The invention provides a synthesis method of high-purity 4-hydroxy-quinoline-2 (1H)-ketone. The method comprises the following steps: heating a compound as shown in a general formula (I) in methanesulfonic acid, cooling a reaction solution to 10-30 DEG C after the reaction is finished, adding water to crystallize, separating and drying to obtain a compound as shown in a general formula (II) with the content of 99.0% or above. According to the synthesis method, generation of by-products of the structure shown in the formula (III) is avoided, the tedious post-treatment purification process is reduced, and the synthesis method is suitable for industrial production.

Method for synthesizing bactericide intermediate

The invention discloses a method for synthesizing a bactericide intermediate. The method comprises the following steps: adding diethyl malonate into a certain amount of aniline for ammonolysis, addingN1,N3-diphenyl malonamide obtained after ammonolysis into polyphosphoric acid for cyclization, carrying out refining after the reaction is completed to obtain 4-hydroxyquinolin-2(1H)-one, performingan amine methylation reaction to obtain 3-[(phenylamino)methylene]-quinoline-2,4(1H,3H)-dione, performing chlorination hydrolysis on the 3-[(phenylamino)methylene]-quinoline-2,4(1H,3H)-dione to obtaina crude product, and carrying out pulping by toluene to obtain the bactericide intermediate. The method provided by the invention has the advantages of easily available raw materials, low cost, simple operation and high yield, and is suitable for industrial production.

Mild, efficient, and solvent-free synthesis of 4-hydroxy-2-quinolinones

Malonic acid monoanilides were obtained in excellent yield from the reaction of anilines with Meldrum's acid under solvent-free conditions. The malonic acid monoanilide intermediates were then treated with methanesulfonic acid anhydride (MSAA) to produce 4-hydroxy-2-quinolinones in excellent yield. It should be noted that both reactions had to be run under mild conditions to avoid the decarboxylation of the malonic acid monoanilide intermediate.