2768-63-0

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2,3-dimethylquinoxaline-5,8-dione serves as a crucial intermediate in the synthesis of various pharmaceuticals and agrochemicals, leveraging its chemical structure to form the backbone of different medicinal and pesticidal agents.
Used as a Marker in EPR Spectroscopy:
In the field of analytical chemistry, 2,3-dimethylquinoxaline-5,8-dione is utilized as a marker in electron paramagnetic resonance (EPR) spectroscopy. Its distinct color and properties make it suitable for detecting a range of free radicals and metal ions, thus playing a significant role in studying reactive species in chemical and biological systems.
Investigated for Organic Electronic Devices:
2,3-dimethylquinoxaline-5,8-dione is being explored for its potential use in organic electronic devices, capitalizing on its electronic properties to enhance the performance of organic semiconductors and other related technologies.
Explored for Photocatalytic Applications:
2,3-dimethylquinoxaline-5,8-dione is under investigation for its possible applications in photocatalysis, where its interaction with light could drive chemical reactions, offering a pathway to develop new methods for environmental remediation and energy production.
Studied for Antioxidant and Anti-inflammatory Properties:
DMQ has been studied for its potential as an antioxidant, which could help in neutralizing harmful free radicals in biological systems. Additionally, its anti-inflammatory properties are of interest, suggesting possible uses in treating conditions affected by inflammation.

Upstream product

• 56183-38-1 5-hydroxy-2,3-dimethylquinoxaline 
• 40328-95-8 2,3-diamino-1,4-dimethoxybenzene 
• 6945-76-2 1,4-dimethoxy-2,3-dinitrobenzene 
• 150-78-7 1,4-dimethoxybezene 
• 19506-22-0 2,3-dimethyl-5,8-dimethoxyquinoxaline 

Downstream Products

• 173912-77-1 2,3-dimethyl-6-<<2-(2-hydroxyphenyl)ethyl>amino>quinoxaline-5,8-dione 
• 14334-07-7 6-(4-chlorophenyl)amino-2,3-dimethyl-5,8-quinoxalinedione 
• 1073276-97-7 2,3-dimethyl-6-(4-ethoxyphenyl)amino-5,8-quinoxalinedione 
• 1073276-99-9 6-(3,4-dichlorophenyl)amino-2,3-dimethyl-5,8-quinoxalinedione 
• 14334-06-6 2,3-dimethyl-6-(4-fluorophenyl)amino-5,8-quinoxalinedione 
• 134755-27-4 2,3-dimethyl-6-<2-(4-hydroxyphenyl)ethylamino>quinoxaline-5,8-dione 

Relevant academic research and scientific papers

Identification of ortho-naphthoquinones as anti-AML agents by highly efficient oxidation of phenols

A straightforward method for synthesizing ortho-naphthoquinones was identified using an easily available cobalt–Schiff base complex. Efficient oxidation of phenols to ortho-naphthoquinones was useful in obtaining compounds with potent biological activity

3D-QSAR studies of heterocyclic quinones with inhibitory activity on vascular smooth muscle cell proliferation using pharmacophore-based alignment

The abnormal proliferation and migration of vascular smooth muscle cells (SMCs) play an important role in the pathology of coronary artery atherosclerosis and restenosis following angioplasty. It was reported that some heterocyclic quinone derivatives such as 6-arylamino-quinoxaline-5,8-diones and 6-arylamino-1H-benzo[d]imidazole-4,7-diones have inhibitory activity on rat aortic smooth muscle cell (RAoSMC) proliferation. To understand the structural basis for antiproliferative activity to design more potent agents, we generated pharmacophore models of representative molecules with high activity using Genetic Algorithm with Linear Assignment of Hypermolecular Alignment of Database (GALAHAD) and aligned a series of compounds to the selected pharmacophore model, then performed three-dimensional quantitative structure-activity relationship (3D-QSAR) studies using Comparative Molecular Field Analysis (CoMFA) and Comparative Molecular Similarity Indices Analysis (CoMSIA). Good cross-validated correlations were obtained with CoMFA (resulting in q2 of 0.734 and r2 of 0.947) and CoMSIA (resulting in q2 of 0.736 and r2 of 0.913). The IC50 values of the heterocyclic quinone derivatives on RAoSMC exhibited a strong correlation with steric and hydrophobic fields of the 3D structure of the molecules, resulting in the reliable prediction of inhibitory activity of the series of compounds.

The aza-analogues of 1,4-naphthoquinones are potent substrates and inhibitors of plasmodial thioredoxin and glutathione reductases and of human erythrocyte glutathione reductase

Various aza-analogues of 1,4-naphthoquinone and menadione were prepared and tested as inhibitors and substrates of the plasmodial thioredoxin and glutathione reductases as well as the human glutathione reductase. The replacement of one to two carbons at the phenyl ring of the 1,4-naphthoquinone core by one to two nitrogen atoms led to an increased oxidant character of the molecules in accordance with both the redox potential values and the substrate efficiencies. Compared to the 1,4-naphthoquinone and menadione, the quinoline-5,8-dione 1 and both quinoxaline-5,8-diones 5 and 6 behaved as the most efficient subversive substrates of the three NADPH-dependent disulfide reductases tested. Modulation of these parameters was observed by alkylation of the aza-naphthoquinone core. The Royal Society of Chemistry.

SYNTHESIS OF 5,8-QUINOXALINEDIONES AND 5,8-QUINAZOLINEDIONES

5,8-Quinoxalinediones (3a-c, 12,13), dibenzophenazine-10,13-diones (5a, b), 5,8-quinazolinediones (17, 23), and 4,5,8(3H)-quinazolinetrione (21) were prepared using oxidative demethylation of the corresponding 5,8-dimethoxy compounds with cerium (IV)

Oxidation of phenols to quinones by bis(trifluoroacetoxy)iodobenzene

Bis (trifluoroacetoxy) iodobenzene oxidizes phenols into quinones in good yield.