70254-44-3

Basic information

• Product Name: quinoline-2,4-diol
• Synonyms: 2-Hydroxyquinolin-4(1H)-one
• CAS NO: 70254-44-3
• Molecular Formula: C₉H₇NO₂
• Molecular Weight: 161.16
• Mol File: 70254-44-3.mol

Chemical Properties

• Melting Point: >330 °C (sublm)(Solv: acetic acid (64-19-7))
• Boiling Point: 303.8±42.0 °C(Predicted)
• Appearance: /
• Density: 1.376±0.06 g/cm3(Predicted)
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: quinoline-2,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: quinoline-2,4-diol(70254-44-3)
• EPA Substance Registry System: quinoline-2,4-diol(70254-44-3)

Safety Data

• Hazardous Substances Data: 70254-44-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
Quinoline-2,4-diol is utilized as a key building block in the synthesis of various pharmaceuticals. Its unique structure allows for the creation of diverse drug molecules with potential therapeutic applications.
Used in Organic Compound Synthesis:
As a versatile chemical compound, quinoline-2,4-diol is employed as a starting material in the synthesis of a wide range of organic compounds, contributing to the development of new chemical entities with specific properties and functions.
Used in Antioxidant Research:
Quinoline-2,4-diol is studied for its potential antioxidant properties, which could be harnessed in the development of novel antioxidants for various applications, including health and industrial settings.
Used in Cancer Research:
quinoline-2,4-diol has been investigated for its ability to inhibit the growth of certain cancer cells, making it a candidate for further research in oncology and the development of anticancer agents.
Used in Material Science:
Quinoline-2,4-diol's unique chemical structure has been explored for its role in the development of new materials, potentially contributing to advancements in material science and technology.
Used in Catalysis:
quinoline-2,4-diol has been studied for its potential use in catalytic systems, which could enhance the efficiency of various chemical reactions and processes in the chemical industry.

Upstream product

• 7218-25-9 1-(Chloroacetyl)-1H-indole-2,3-dione 
• 7732-18-5 water 
• 91-22-5 quinoline 
• 606-23-5 1H-indene-1,3(2H)-dione 
• 20628-20-0 ethyl N-acetylanthranilate 
• 15580-32-2 malonanilic acid 
• 6140-13-2 (2-acetylphenyl)carbamic acid ethyl ester 
• 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 
• 108-98-5 thiophenol 
• 86795-52-0 2-Oxo-3-phenyliodonium-1,2-dihydrochinolin-4-olat 

Downstream Products

• 40335-01-1 2-methoxy-1-methyl-1H-quinolin-4-one 
• 32262-18-3 N-methyl-4-methoxyquinolin-2(1H)-one 
• 529-89-5 2,4-dihydroxy-quinoline-3-carbaldehyde 
• 40742-41-4 3-(4-nitro-phenylazo)-quinoline-2,4-diol 
• 6407-80-3 3-phenylazo-quinoline-2,4-diol 
• 40742-49-2 3-p-tolylazo-quinoline-2,4-diol 
• 38777-53-6 3-(3-nitro-phenylazo)-quinoline-2,4-diol 
• 26138-65-8 3-benzoyl-2,4-dihydroxyquinoline 
• 26138-64-7 3-acetyl-2,4-dihydroxyquinoline 
• 6628-93-9 4-anilino-quinolin-2-ol 
• 110216-87-0 4-amino-quinolin-2-ol 
• 20151-40-0 2,4-dibromoquinoline 
• 14933-24-5 3-bromo-quinoline-2,4-diol 
• 15151-57-2 2,4-dihydroxy-3-nitroquinoline 

Relevant articles and documents

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.

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.

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.

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.

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.

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.

Synthesis and colon anticancer activity of some novel thiazole/-2-quinolone derivatives

We direct for the synthesis of 1,6,7-trisubstituted-4-phenylthiazol-2(3H)-ylidene)hydrazono)methyl)quinolin-2-one derivatives by the reaction of corresponding thiosemicarbazone derived by 2-quinolone derivatives with 2-bromoacetophenones in presence of triethylamine at room temperature. The mechanism of the formed products was discussed. The structure of the obtained products was fully characterized using different spectral techniques including infrared (IR), nuclear magnetic resonance (NMR), and mass spectrometry (MS) together with elemental analyses. The new synthesized compounds showed a moderate colon anticancer activity.

Arylidenes of Quinolin-2-one scaffold as Erlotinib analogues with activities against leukemia through inhibition of EGFR TK/ STAT-3 pathways

A new series of 6-substiuted-4-(2-(4-substituted-benzylidene)hydrazinyl)quinolin-2(1H)-one derivatives have been designed and synthesized. The structure of the synthesized compounds was proved by 1H NMR, 13C NMR, 2D NMR, mass and elemental analyses. The target compounds were evaluated for their in vitro cytotoxic activity against 60 cancer cell lines according to NCI protocol. Consequently, the most active compounds were further examined against the most sensitive leukemia RPMI-8226 and on healthy cell lines. 6-Chloro-derivative was the most active one; with IC50 = 15.72 ± 1.21 and 46.05 ± 2.36 μM against RPMI-8226 and normal cell lines, respectively. Also, it showed a remarkable inhibitory activity compared to gefitinib on the EGFR TK mutant, wild and on H-RAS in addition to STAT-3 with IC50 = 695.49 ± 21.8, 263.15 ± 15.13, 10.61 ± 0.27 and 1.753 ± 0.81 nM, respectively. Cell cycle analysis of RPMI-8226 cells treated with the 6-chloro-derivative showed cell cycle arrest at G2/M phase (supported by Caspases-3,8, BAX and Bcl-2 studies) with a significant pro-apoptotic activity as indicated by annexin V-FITC staining. Moreover, the docking studies ROCS analysis and Tanimoto scores supported the results. The study illustrated the effect of several factors on compounds activity.