34982-01-9

Usage

Uses

Used in Pharmaceutical Industry:
6-hydroxy-4-methyl-1H-quinolin-2-one is used as a building block for the synthesis of various pharmaceuticals and bioactive molecules. Its unique structure allows for the development of new drugs with improved efficacy and selectivity.
Used in Anti-inflammatory Applications:
6-hydroxy-4-methyl-1H-quinolin-2-one is used as an anti-inflammatory agent due to its ability to modulate inflammatory pathways and reduce the production of pro-inflammatory mediators. This makes it a promising candidate for the treatment of inflammatory diseases such as arthritis and inflammatory bowel disease.
Used in Antioxidant Applications:
6-hydroxy-4-methyl-1H-quinolin-2-one is used as an antioxidant, as it can neutralize reactive oxygen species and protect cells from oxidative damage. Its antioxidant properties make it a potential candidate for the prevention and treatment of various oxidative stress-related disorders.
Used in Neuroprotective Applications:
6-hydroxy-4-methyl-1H-quinolin-2-one is used as a neuroprotective agent, as it has been found to protect neurons from damage and degeneration. Its neuroprotective properties make it a promising candidate for the treatment of neurological disorders such as Alzheimer's disease and Parkinson's disease.
Used in Cancer Therapy:
6-hydroxy-4-methyl-1H-quinolin-2-one is used as an anti-cancer agent, as it has shown potential in inhibiting the growth and proliferation of cancer cells. Its ability to target specific molecular pathways involved in cancer progression makes it a promising candidate for the development of novel cancer therapies.

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 
• 1597709-99-3 4-[(2-chloro-6-hydroxy-4-methylquinolin-5-yl)methyl]-5-(4-methylphenyl)-2,3-dihydro-1H-pyrazol-3-one 
• 1597710-18-3 8-chloro-10-methyl-2-(4-methylbenzoyl)-3H-chromeno[6,5-b]pyridin-3-one 

Relevant academic research and scientific papers

Design and synthesis of novel coumarin analogs and their nematicidal activity against five phytonematodes

The presence of hydroxyl groups at the C4 and C7 positions in coumarin backbone has been proposed as a potential modification site for providing excellent bioactivity according to previous studies. A series of novel coumarin derivatives were rationally designed and synthesized by use of a complex catalytic system for a targeted modification at the above sites. These derivatives were assayed for nematicidal activity. As predicted, the derivatization enhanced the activity of the coumarins against five nematodes. Compounds 7b, 9a, 10c and 11c showed significant strong nematicidal broad spectrum activity against all tested nematodes. Compound 10c was the most effective with the lowest LC50 values against Meloidogyne incognita (5.1 μmol/L), Ditylenchus destructor (3.7 μmol/L), Bursaphelenchus mucronatus (6.4 μmol/L), Bursaphelenchus B. xylophilus (2.5 μmol/L) and Aphelenchoides besseyi (3.1 μmol/L), respectively. A brief investigation on the structure-activity relationships (SAR) revealed that the targeted modification by a C7 hydroxyl was optimum compared with that of a C4 hydroxyl and that the coupling chain length was crucial for the nematicidal activity.

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.

Ruthenium-catalyzed cyclization of anilides with substituted propiolates or acrylates: An efficient route to 2-quinolinones

A Ru-catalyzed cyclization of anilides with propiolates or acrylates affording 2-quinolinones having diverse functional groups in good to excellent yields is described. Later, 2-quinolinones were converted into 3-halo-2-quinolinones and 2-chloroquinolines

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.