34982-01-9

Basic information

• Product Name: 6-hydroxy-4-methyl-1H-quinolin-2-one
• Synonyms: 6-hydroxy-4-methyl-1H-quinolin-2-one;4-Methylquinoline-2,6-diol;6-hydroxy-4-Methylquinolin-2(1H)-one
• CAS NO: 34982-01-9
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18
• Mol File: 34982-01-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 437.2°Cat760mmHg
• Flash Point: 218.2°C
• Appearance: /
• Density: 1.264g/cm³
• Vapor Pressure: 2.96E-08mmHg at 25°C
• Refractive Index: 1.611
• CAS DataBase Reference: 6-hydroxy-4-methyl-1H-quinolin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-hydroxy-4-methyl-1H-quinolin-2-one(34982-01-9)
• EPA Substance Registry System: 6-hydroxy-4-methyl-1H-quinolin-2-one(34982-01-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 34982-01-9(Hazardous Substances Data)

Usage

General Description

6-hydroxy-4-methyl-1H-quinolin-2-one is a chemical compound with the molecular formula C10H9NO2. It is a derivative of quinolin-2-one and contains a hydroxy and methyl group on the aromatic ring. 6-hydroxy-4-methyl-1H-quinolin-2-one is used in the pharmaceutical industry as a building block for the synthesis of various pharmaceuticals and bioactive molecules. It has also been found to exhibit anti-inflammatory, antioxidant, and neuroprotective properties, making it a promising candidate for potential therapeutic applications. Additionally, it has been studied for its potential in treating certain neurological disorders and as an anti-cancer agent.

InChI:InChI=1/C10H9NO2/c1-6-4-10(13)11-9-3-2-7(12)5-8(6)9/h2-5,12H,1H3,(H,11,13)

Upstream product

• 5342-23-4 6-methoxy-4-methyl-2-oxo-1H-quinoline 
• 19213-10-6 acetoacetic acid-(4-hydroxy-anilide) 
• 4341-76-8 Ethyl 2-butynoate 
• 103-90-2 4-acetaminophenol 
• 104-94-9 4-methoxy-aniline 
• 5437-98-9 4'-methoxyacetoacetanilide 

Downstream Products

• 4363-99-9 2,6-dihydroxy-quinoline-4-carboxylic acid 
• 75588-21-5 4-Methyl-6-(4-phenylsulfinyl-butoxy)-carbostyril 
• 75588-24-8 4-Methyl-6-(4-phenylsulfonyl-butoxy)-carbostyril 
• 73290-55-8 4-Methyl-6-{3-[4-(4-tert.-butyl-benzyl)-piperazin-1-yl]-propoxy}-2-oxo-1,2-dihydroquinoline 
• 1207862-96-1 methyl 3-[(4-methyl-2-oxo-1,2-dihydro-6-quinolinyl)oxy]methylbenzoate 
• 1597710-18-3 8-chloro-10-methyl-2-(4-methylbenzoyl)-3H-chromeno[6,5-b]pyridin-3-one 
• 1597709-99-3 4-[(2-chloro-6-hydroxy-4-methylquinolin-5-yl)methyl]-5-(4-methylphenyl)-2,3-dihydro-1H-pyrazol-3-one 

Relevant articles and documents

Discovery, synthesis and molecular substantiation of N-(benzo[d]thiazol-2-yl)-2-hydroxyquinoline-4-carboxamides as anticancer agents

The effort was taken to develop a series of benzothiazole and quinoline fused bioactive compounds obtained through a four-step synthetic route using a range of substituted acetoacetanilides. Achieved N-(benzo[d]thiazol-2-yl)-2-hydroxyquinoline-4-carboxamides (6a-l) were produced up to 96% of yield while the eco-friendly p-TSA used as a catalyst. Further, the anticancer activity of these compounds was determined using a range of cancer cell lines starting from MCF-7 (Breast cancer), HCT-116 (Colon cancer), PC-3 & LNCaP (Prostate) and SK-HEP-1 (Liver cancer). Present study compounds were also testified for antioxidant properties prior to anticancer studies since the Reactive Oxygen Species (ROS) being vital in cancer development. To determine the cell membrane stability effects of the compounds, human red blood cells (HRBC) based membrane protection assay was determined. In the results, compounds 6a-l were able to produce a dominated result values over PC3 cell lines (Prostate cancer) than the other cell lines used in this study. Since the connectivity of human germ cell alkaline phosphatase (hGC-ALP) in the development of prostate cancer is known, the most active compounds were evaluated for the hGC-ALP inhibition in order to ensure a mechanism of anticancer action of these compounds. The mode of interaction and binding affinity of these compounds was also investigated by a molecular docking study. In the results, 6d, 6i, 6k, and 6l were found with least IC50 values 0.075 μM and highest relative activity of 92%, 90%, and 96% respectively. The need for further animal model evaluation and pre-clinical studies recognized.

Characterization of 4-methyl-2-oxo-1,2-dihydroquinolin-6-yl acetate as an effective antiplatelet agent

We have studied earlier a membrane bound novel enzyme Acetoxy Drug: protein transacetylase identified as Calreticulin Transacetylase (CRTAase) that catalyzes the transfer of acetyl groups from polyphenolic acetates (PAs) to the receptor proteins and thus modulating their biological activities. In this communication, we have reported for the first time that acetoxy quinolones are endowed with antiplatelet action by virtue of causing CRTAase catalyzed activation of platelet Nitric Oxide Synthase (NOS) by way of acetylation leading to the inhibition of ADP/Arachidonic acid (AA)-dependent platelet aggregation. The correlation of specificity of platelet CRTAase to various analogues of acetoxy quinolones with intracellular NO and consequent effect on inhibition of platelet aggregation was considered crucial. Among acetoxy quinolones screened, 6-AQ (4-methyl-2-oxo-1,2-dihydroquinolin-6-yl acetate/6-acetoxyquinolin-2-one, 22) was found to be the superior substrate to platelet CRTAase and emerged as the most active entity to produce antiplatelet action both in vitro and in vivo. 6-AQ caused the inhibition of cyclooxygenase-1 (Cox-1) resulting in the down regulation of thromboxane A2 (TxA2) and the inhibition of platelet aggregation. Structural modification of acetoxy quinolones positively correlated with enhancement of intracellular NO and antiplatelet action.