6639-79-8

Usage

Uses

Used in Pharmaceutical Industry:
6-Chloroquinoxaline-2,3-diol is used as a glycine receptor antagonist for its potential therapeutic effects in various conditions. It is being investigated for its use as an analgesic, anticonvulsant, neuroprotectant, and sedative-hypnotic.
As an Analgesic:
6-Chloroquinoxaline-2,3-diol is used to alleviate pain by blocking glycine receptors, which play a role in pain transmission in the central nervous system. By inhibiting these receptors, it can help reduce pain signals and provide relief to patients.
As an Anticonvulsant:
6-CHLORO-2,3-DIOXO-1,2,3,4-TETRAHYDROQUINOXALINE is also being studied for its potential use as an anticonvulsant, which can help prevent or reduce the severity of seizures in patients with epilepsy or other seizure disorders. Its glycine receptor antagonist properties may contribute to its anticonvulsant effects.
As a Neuroprotectant:
6-Chloroquinoxaline-2,3-diol has the potential to act as a neuroprotectant, which means it can help protect neurons from damage or degeneration. This property may be useful in the treatment of neurodegenerative diseases such as Alzheimer's, Parkinson's, or multiple sclerosis.
As a Sedative-Hypnotic:
In addition to its other potential uses, 6-chloroquinoxaline-2,3-diol is being investigated for its use as a sedative-hypnotic. This means it may help induce sleep or promote relaxation in patients with insomnia or other sleep disorders. Its effects on glycine receptors could contribute to its sedative and hypnotic properties.

InChI:InChI=1/C8H5ClN2O2/c9-4-1-2-5-6(3-4)11-8(13)7(12)10-5/h1-3H,(H,10,12)(H,11,13)

Upstream product

• 5448-43-1 6-chloroquinoxaline 
• 6639-80-1 6-chloroquinoxaline 1,4-dioxide 
• 95-83-0 4-Chloro-1,2-phenylenediamine 
• 95-92-1 oxalic acid diethyl ester 
• 144-62-7 oxalic acid 
• 89-63-4 4-Chloro-2-nitroaniline 
• 64-18-6 formic acid 
• 7722-84-1 dihydrogen peroxide 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 15804-19-0 quinoxaline-2,3-dione 
• 34836-97-0 6-chloro-1,2-dihydro-2-oxoquinoxaline 4-oxide 
• 34797-69-8 p-chloro-o-nitroacetoacetanilide 
• 89-61-2 2,5-dichloronitrobenzene 

Downstream Products

• 2958-87-4 2,3,6-trichloro-quinoxaline 
• 73855-45-5 6-chloro-1,2,3,4-tetrahydroquinoxaline 
• 91896-68-3 (8-Chloro-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)-((S)-1-methyl-2-phenyl-ethyl)-amine 
• 91925-59-6 (8-Chloro-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)-((R)-1-methyl-2-phenyl-ethyl)-amine 
• 91896-21-8 CP 66278 
• 127710-80-9 8-Chloro-1-(4-chloro-phenyl)-[1,2,4]triazolo[4,3-a]quinoxalin-4-ylamine 
• 91896-57-0 CP 66713 
• 127710-79-6 8-Chloro-1-phenyl-4-piperazin-1-yl-[1,2,4]triazolo[4,3-a]quinoxaline 
• 127710-76-3 (8-Chloro-1-trifluoromethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)-cyclohexyl-amine 
• 91896-54-7 8-chloro-4-diethylamino-1-phenyl-[1,2,4]triazolo[4,3-a]quinoxaline 
• 91896-46-7 8-chloro-4-isopropylamino-1-phenyl-[1,2,4]triazolo[4,3-a]quinoxaline 
• 127710-60-5 (8-Chloro-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)-phenyl-amine 
• 91896-47-8 8-chloro-4-ethylamino-1-phenyl-[1,2,4]triazolo[4,3-a]quinoxaline 
• 127710-59-2 (8-Chloro-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)-cyclohexyl-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.

Synthesis method of 2,3-dihydroxy-6-chloroquinoxaline

The invention relates to a synthetic method of 2,3-dihydroxy-6-chloroquinoxaline, and belongs to the technical field of organic synthesis. The synthesis method comprises the following synthesis steps:(1) adding 4-chloro-o-phenylene diamine, diethyl oxalate and an alkali into a reaction flask, controlling a reaction system to be at a negative pressure, and heating a reaction solution to reflux tostart a reaction; (2) after the reaction is finished, adding active carbon for de-coloration, and performing hot filtration to obtain filtrate I; (3) cooling the filtrate I obtained in the step (2) to0-5 DEG C, crystallizing for 1-2 hours, and filtering to obtain a filter cake. The method has the advantages that (1) the side reactions are reduced by reducing the reaction temperature; (2) the reaction substrate is activated by using an alkali, so that the reaction is promoted; (3) a byproduct namely ethanol is extracted through rectification to promote forward proceeding of the reaction, so that the reaction time is shortened; and (4) the product quality is improved, and a 2,3-dihydroxy-6-chloroquinoxaline standard substance meeting the requirements is obtained.

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.

Rationalization of benzazole-2-carboxylate versus benzazine-3-one/ benzazine-2,3-dione selectivity switch during cyclocondensation of 2-aminothiophenols/phenols/anilines with 1,2-biselectrophiles in aqueous medium

The cyclocondensation reaction of 2-aminothiophenols with 1,2-biselectrophiles such as ethyl glyoxalate and diethyl oxalate in aqueous medium leads to the formation of benzothiazole-2-carboxylates via the 5-endo-trig process contrary to Baldwin's rule. On the other hand, the reaction of 2-aminophenols/anilines produced the corresponding benzazine-3-ones or benzazine-2,3-diones via the 6-exo-trig process in compliance with Baldwin's rule. The mechanistic insights of these cyclocondensation reactions using the hard-soft acid-base principle, quantum chemical calculations (density functional theory), and orbital interaction studies rationalize the selectivity switch of benzothiazole-2-carboxylates versus benzazine-3-ones/ benzazine-2,3-diones. The presence of water facilitates these cyclocondensation reactions by lowering of the energy barrier.

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.

A new facile, efficient synthesis and structure peculiarity of quinoxaline derivatives with two benzimidazole fragments

A highly efficient and versatile method for the synthesis of quinoxaline derivatives with two benzimidazole fragments have been developed on the basis of the ring contraction of 3-(benzimidazo-2-yl)quinoxalin-2(1H)-one with 1,2-diaminobenzene and its various types of substituted and condensed derivatives. Owing to the inter- and intramolecular processes, involving self association, proton exchange, conformational, and/or tautomeric exchanges between several forms for most of the bis-benzimidazolylquinoxalines signals of bridged and neighboring carbon atoms and the hydrogen atoms of the neighboring carbon atoms of benzimidazole fragments in the NMR spectra are broadened. The conjugation between the benzimidazole fragments and the quinoxaline core of the molecules is increased from the quinoxaline derivative (10c) to its thiadiazol[f]- (17) and pyrrolo[a]-(19) annulated derivatives, resulting in a greater planarity of the molecule as a whole.

A direct method for oxidizing quinoxaline, tetraazaphenanthrene, and hexaazatriphenylene moieties using hypervalent λ3-iodinane compounds

An efficient oxidation reaction of various electron-poor quinoxaline-core-containing compounds, such as quinoxalines, 1,4,5,8-tetraazaphenanthrenes, and 1,4,5,8,9,12-hexaazatriphenylene, using [bis(trifluoroacetoxy)iodo]benzene is reported. These compounds are converted into the corresponding quinoxalinediones in good to high yields at room temperature using an acetonitrile/water solvent mixture. This unprecedented reaction should enable the synthesis of a wide variety of compounds useful in several fields of chemistry.

HETEROCYCLIC INHIBITORS OF HISTAMINE RECEPTORS FOR THE TREATMENT OF DISEASE

The present invention relates to compounds and methods which may be useful as inhibitors of H1R and/or H4R for the treatment or prevention of inflammatory, autoimmune, allergic, and ocular diseases.

HETEROCYCLIC INHIBITORS OF HISTAMINE RECEPTORS FOR THE TREATMENT OF DISEASE

The present invention relates to compounds and methods which may be useful as inhibitors of H1R and/or H4R for the treatment or prevention of inflammatory, autoimmune, allergic, and ocular diseases.