2379-60-4

Usage

Uses

Used in Organic Synthesis:
2,3-DICHLORO-6-NITROQUINOXALINE is used as a building block for the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new compounds with potential therapeutic and agricultural applications.
Used in Molecular Electronics:
2,3-DICHLORO-6-NITROQUINOXALINE is used as a reagent in molecular electronics due to its ability to undergo reversible electron transfer reactions, which is crucial for the development of advanced electronic devices and materials.
Used in Electrochromic Materials:
2,3-DICHLORO-6-NITROQUINOXALINE is used as a component in the development of electrochromic materials, which can change color in response to an electric field, finding applications in smart windows and displays.
Used in Redox-Active Materials:
2,3-DICHLORO-6-NITROQUINOXALINE is used in the development of redox-active materials, which are important for energy storage and conversion technologies, such as batteries and fuel cells.
Used in Antimicrobial Applications:
2,3-DICHLORO-6-NITROQUINOXALINE is used as a potential antibacterial and antiviral agent, leveraging its nitro group and chloro substituents, which are known to possess antimicrobial properties, for the development of new treatments against infectious diseases.

InChI:InChI=1/C8H3Cl2N3O2/c9-7-8(10)12-6-3-4(13(14)15)1-2-5(6)11-7/h1-3H

Upstream product

• 2379-56-8 2,3-dihydroxy-6-nitroquinoxaline 
• 91-19-0 2,3-diethynylquinoxaline 
• 15804-19-0 2,3-dihydroxyquinoxaline 
• 15804-19-0 quinoxaline-2,3-dione 
• 95-54-5 1,2-diamino-benzene 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 2379-56-8 6-nitro-1,2,3,4-tetrahydroquinoxaline-2,3-dione 

Downstream Products

• 35252-30-3 (6-nitro-3-m-tolyl-3H-thiazolo[4,5-b]quinoxalin-2-ylidene)-m-tolyl-amine 
• 35252-26-7 (6-nitro-3-o-tolyl-3H-thiazolo[4,5-b]quinoxalin-2-ylidene)-o-tolyl-amine 
• 35251-90-2 (3-chloro-phenyl)-[3-(3-chloro-phenyl)-6-nitro-3H-thiazolo[4,5-b]quinoxalin-2-ylidene]-amine 
• 35251-94-6 (2-methoxy-phenyl)-[3-(2-methoxy-phenyl)-6-nitro-3H-thiazolo[4,5-b]quinoxalin-2-ylidene]-amine 
• 31102-73-5 (4-bromo-phenyl)-(6-nitro-thiazolo[4,5-b]quinoxalin-2-yl)-amine 
• 31102-86-0 3-(4-bromo-phenyl)-6-nitro-3H-thiazolo[4,5-b]quinoxalin-2-ylideneamine 
• 31102-75-7 (2-ethoxy-phenyl)-(6-nitro-thiazolo[4,5-b]quinoxalin-2-yl)-amine 
• 31102-88-2 3-(2-ethoxy-phenyl)-6-nitro-3H-thiazolo[4,5-b]quinoxalin-2-ylideneamine 
• 35251-92-4 (4-bromo-phenyl)-[3-(4-bromo-phenyl)-6-nitro-3H-thiazolo[4,5-b]quinoxalin-2-ylidene]-amine 
• 35242-74-1 (6-nitro-3-phenyl-3H-thiazolo[4,5-b]quinoxalin-2-ylidene)-phenyl-amine 
• 31102-87-1 3-(2-methoxy-phenyl)-6-nitro-3H-thiazolo[4,5-b]quinoxalin-2-ylideneamine 
• 31102-74-6 (2-methoxy-phenyl)-(6-nitro-thiazolo[4,5-b]quinoxalin-2-yl)-amine 
• 35251-87-7 (4-chloro-phenyl)-[3-(4-chloro-phenyl)-6-nitro-3H-thiazolo[4,5-b]quinoxalin-2-ylidene]-amine 
• 31102-72-4 (4-chloro-phenyl)-(6-nitro-thiazolo[4,5-b]quinoxalin-2-yl)-amine 

Relevant academic research and scientific papers

Novel molecular targeting anti-tumor aza-steroid derivative based on lipid toxicity and preparation and application thereof

The invention provides a novel molecular targeting anti-tumor aza-steroid derivative based on lipid toxicity and a preparation method and application thereof, and belongs to the field of chemical medicines. The derivative is a compound as shown in a formula I, or a salt thereof, or a stereoisomer thereof. The compound is low in toxicity or basically non-toxic to normal cells, has an obvious inhibition effect to tumor cell lines, particularly has good lipid toxicity selectivity to tumor cells such as liver cancer, lung cancer and the like in vivo, and has an obvious inhibition effect; meanwhile, the compound can effectively activate SREBP1 and PPAR gamma, inhibit lipid transport MTTP, cause lipid aggregation in tumor cells and cause lipid toxicity of the tumor cells. The compound can be used for treating liver cancer, lung cancer and the like in a molecular targeting manner, is low in toxicity or even non-toxic, and has a good application prospect.

Facile synthesis and anti-proliferative activity evaluation of quinoxaline derivatives

A series of “drug-like” compounds based on quinoxaline scaffold with arylsulfonyl hydrazinyl, arylformyl hydrazinyl or arylsulfonyl groups at C-2 and aryloxy groups at C-3, were synthesized in 4 or 5 steps involving cyclization, chlorination and coupling reactions. Cellular anti-proliferative activities of these quinoxaline derivatives in vitro were determined, which revealed that the inhibitory potency and selectivity of 6f was comparable to that of the positive control.

Novel [1,2,4]Triazolo[4,3-a]Quinoxaline Derivative, Method For Preparing Same, And Pharmaceutical Composition For Preventing Or Treating BET Protein-Related Diseases, Containing Same As Active Ingredient

Provided are a novel [1,2,4]triazolo[4,3-a]quinoxaline derivative, a method for preparing the same, and a pharmaceutical composition for preventing or treating bromodomain extra-terminal (BET) protein-related diseases including cancer and autoimmune disea

A One-pot Facile Synthesis of 2,3-Dihydroxyquinoxaline and 2,3-Dichloroquinoxaline Derivatives Using Silica Gel as an Efficient Catalyst

An efficient one-pot reaction has been developed for the synthesis of 2,3-dichloroquinoxaline derivatives 3a–n. The reaction was performed in two steps via a silica gel catalyzed tandem process from o-phenylenediamine and oxalic acid, followed by addition of phosphorus oxychloride (POCl3). A variety of 2,3-dichloroquinoxalines have been obtained in good to excellent overall yields. Eight known compounds 3a–3h were characterized by IR, 1H-NMR, and mass spectroscopies. Compounds 3i–3n without spectroscopic data were characterized by IR, 1H-NMR, 13C-NMR, and mass spectroscopies.

Method for preparing 2,3-dichloro-quinoxaline derivative through one-pot procedure

The invention belongs to the field of drug synthesis, and specifically relates to a new method for preparing 2,3-dichloro-quinoxaline derivative through one-pot procedure. According to the method, cheap o-phenylenediamine and oxalic acid are adopted as raw materials, and the cheap and easily available and environmentally friendly silica gel or methanesulfonic acid is adopted as a catalyst while steps of intermediate separation and purification are omitted; the method has the advantages of easiness in operation, low cost, mild reaction conditions and environmental friendliness and promotes industrial mass production.

A new solvent for the reaction of chlorination of hydroxyquinoxaline derivatives with vilsmeier reagent

A new efficient procedure for the chlorination of hydroxyquinoxaline derivatives into the corresponding chlorides is described. It has been found that the use of 1-chlorobutane produces the highest yield, reduces the time of reaction and facilitates direct formation of crystals without any purification.

Synthesis, structural, catecholase, tyrosinase and DFT studies of pyrazoloquinoxaline derivatives

Six functional multidentate ligands: 2,3-bis(3,5-dimethyl-1H-pyrazol-1-yl) quinoxaline, L1, 2,3-bis(3,5-dimethyl-1H-pyrazol-1-yl)-6-nitroquinoxaline, L2, 2,3-bis(3,5-dimethyl-1H-pyrazol-1-yl)-6-methylquinoxaline, L3, 2-(3,5-dimethyl-1H-pyrazol-1-yl)-3-hydrazinyl-6-nitroquinoxaline L4, 2-chloro-3-(3,5-dimethyl-1H-pyrazol-1-yl)-6-methylquinoxaline, L5, 2-chloro-3-(3,5-dimethyl-1H-pyrazol-1-yl) quinoxaline, L6, and a new copper (II) complex, were prepared and evaluated for their catecholase activities at aerobic conditions. We found that, the reaction rate depends on: The nature of the substituents in the quinoxaline ring, counter anion, metal, concentration of ligand and the used solvent. The complex obtained in-situ from reaction of one equivalent of ligand L1 and two equivalents of Cu(CH3COO)2 in methanol showed the highest oxidation rate activity (V?=?33.48?μmol?L?1. min?1). In addition, geometry optimizations of the complexes in order to get better insight into the geometry and the electronic structure and chemical reactivity were carried out by means of DFT calculations.

Synthesis of a visibly emissive 9-nitro-2,3-dihydro-1H-pyrimido[1,2-a]quinoxalin-5-amine scaffold with large stokes shift and live cell imaging

We have developed a novel fluorescent scaffold 4 which is a 9-nitro-2,3-dihydro-1H-pyrimido[1,2-a]quinoxalin-5-amine derivative from the reaction between di-tert-butyl but-2-ynedioate and a quinoxaline molecule containing a dimethyl amine side tail in high yield. The synthesis of scaffold 4 involves an sp3 C-N bond cleavage mechanism which is not very common. The scaffolds 4 is emissive in the visible range λem ～ (517-540) nm with large stokes shifts (5005-6378) cm-1 in ethanol. Laser confocal microscopy of the live HepG2 cells treated with compound 4f shows that it can be used for live cell imaging in nanomolar concentrations.

A new small molecule inhibitor of soluble guanylate cyclase

Soluble guanylate cyclase (sGC) is a haem containing enzyme that regulates cardiovascular homeostasis and multiple mechanisms in the central and peripheral nervous system. Commonly used inhibitors of sGC activity act through oxidation of the haem moiety, however they also bind haemoglobin and this limits their bioavailability for in vivo studies. We have discovered a new class of small molecule inhibitors of sGC and have characterised a compound designated D12 (compound 10) which binds to the catalytic domain of the enzyme with a KD of 11 μM in a SPR assay.

Design, synthesis and biological evaluation of type-II VEGFR-2 inhibitors based on quinoxaline scaffold

In an effort to develop ATP-competitive VEGFR-2 selective inhibitors, a series of new quinoxaline-based derivatives was designed and synthesized. The target compounds were biologically evaluated for their inhibitory activity against VEGFR-2. The design of the target compounds was accomplished after a profound study of the structure activity relationship (SAR) of type-II VEGFR-2 inhibitors. Among the synthesized compounds, 1-(2-((4-methoxyphenyl)amino)-3- oxo-3,4 dihydroquinoxalin-6-yl)-3-phenylurea (VIIa) displayed the highest inhibitory activity against VEGFR-2. Molecular modeling study involving molecular docking and field alignment was implemented to interpret the variable inhibitory activity of the newly synthesized compounds.