91895-65-7

Upstream product

• 97111-34-7 C₂₅H₂₃ClN₆ 
• 97111-40-5 2-chloro-3-(2'-benzylidenehydrazino)quinoxaline 
• 100-52-7 benzaldehyde 
• 51347-93-4 2‐chloro‐3‐hydrazinylquinoxaline 
• 1663-61-2 triethoxymethylbenzene 
• 97111-35-8 C₂₁H₁₅ClN₆ 
• 95-54-5 1,2-diamino-benzene 
• 15804-19-0 quinoxaline-2,3-dione 
• 2213-63-0 2,3-dichloroquinoxaline 

Downstream Products

• 91895-66-8 4-diethylamino-1-phenyl-[1,2,4]triazolo[4,3-a]quinoxaline 
• 129227-28-7 1-phenyl-[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one 

Relevant academic research and scientific papers

Compound and application thereof

The invention relates to a compound and an application thereof. The compound has a structure as shown in a formula I. The compound takes quinoxaline triazole as a parent nucleus, so that the compound has higher electron deficiency performance, and electro

Discovery of novel [1,2,4]triazolo[4,3-a]quinoxaline aminophenyl derivatives as BET inhibitors for cancer treatment

Bromodomain and extra-terminal (BET) proteins, a class of epigenetic reader domains has emerged as a promising new target class for small molecule drug discovery for the treatment of cancer, inflammatory, and autoimmune diseases. Starting from in silico screening campaign, herein we report the discovery of novel BET inhibitors based on [1,2,4]triazolo[4,3-a]quinoxaline scaffold and their biological evaluation. The hit compound was optimized using the medicinal chemistry approach to the lead compound with excellent inhibitory activities against BRD4 in the binding assay. The substantial antiproliferative activities in human cancer cell lines, promising drug-like properties, and the selectivity for the BET family make the lead compound (13) as a novel BRD4 inhibitor motif for anti-cancer drug discovery.

Formation of 1-phenyl-4-oxo [1,2,4]triazolo[4,3-a]quinoxaline from 2- chloro-3-(2'-benzylidenehydrazino)quinoxaline during dehydrogenative cyclisation using cupric acetate

Attempted dehydrogenative cyclisation of 2-chloro-3-(2'- benzylidinchydrazino)quinoxaline 5 with a view to prepare 1-phenyl-4-chloro- [1,2,4]-triazolo [4, 3-a]quinoxaline 6 using cupric acetate gives 1-phenyl-4- oxo-[1,2,4]triazolo[4,3-a]quinoxaline 7. A rational explanation is offered for this reaction and the applicability of cupric acetate as dehydrogenative cyclisation agent (such as in the conversion of 10→11) has been demonstrated.

4-Aminotriazoloquinoxalines. A Novel Class of Potent Adenosine Receptor Antagonists and Potential Rapid-Onset Antidepressants

A series of 4-aminotriazoloquinoxalines has been prepared.Many compounds from this class reduce immobility in Porsolt's behavioral despair model in rats upon acute administration and may therefore have therapeutic potential as novel and rapid acting antidepressant agents.Optimal activity in this test is associated with hydrogen, CF3, or small alkyl groups in the 1-position, with NH2, NH-acetyl, or amines substituted with small alkyl groups in the 4-position, and with hydrogen or 8-halogen substituents in the aromatic ring.Furthermore, many of these 4-aminoquinoxalines bind avidly, and in some cases very selectively, to adenosine A1 and A2 receptors.A1 affinity of these compounds was measured by their inhibition of tritiated CHA (N6-cyclohexyladenosine) binding in rat cerebral cortex membranes and A2 affinity by their inhibition of tritiated NECA (5'-(N-ethylcarbamoyl)adenosine) binding to rat striatal homogenate in the presence of cold N6-cyclopentyladenosine.Structure-activity relationship (SAR) studies show that best A1 affinity is associated with ethyl, CF3, or C2F5 in the 1-position, NH-iPr or NH-cycloalkyl in the 4-position, and with an 8-chloro substituent.Affinity at the A2 receptor is mostly dependent on the presence of an NH2 group in the 4-position and is enhanced by phenyl, CF3, or ethyl in the 1-position.The most selective A1 ligand by a factor of >3000 is 121 (CP-68,247; 8-chloro-4-(cyclohexylamino)-1-(trifluoromethyl)triazoloquinoxaline) with an IC50 of 28 nM at the A1 receptor.The most potent A2 ligand is 128 (CP-66,713; 4-amino-8-chloro-1-phenyltriazoloquinoxaline) with an IC50 of 21 nM at the A2 receptor and a 13-fold selectivity for this receptor.Representatives from this series appear to act as antagonists at both A1 and A2 receptors since they antagonize the inhibiting action of CHA on norepinephrine-stimulated cAMP formation in fat cells and they decrease cAMP accumulation induced by adenosine in limbic forebrain slices.Thus certain members of this 4-aminotriazoloquinoxaline series are among the most potent and A1 or A2 selective non-xanthine adenosine antagonists known.

Method of using [1,2,4]triazolo[4,3-a]quinoxaline-4-amine derivatives as antidepressant and antifatigue agents

A series of novel [1,2,4]triazolo[4,3-a]quinoxaline-4-amine derivatives wherein the amine group is optionally substituted with lower alkyl, phenylalkyl having up to three carbon atoms in the alkyl moiety or alkanoyl having from two to five carbon atoms, or the amine group alternatively completes a piperazino ring, the quinoxaline ring is optionally substituted with fluorine, chlorine, bromine or methoxy, and the triazolo ring is optionally substituted with lower alkyl, lower perfluoroalkyl or phenyl are disclosed. These novel compounds are useful for treatment of symptoms associated with depression. Also disclosed are pharmaceutical compositions containing the novel compounds of this invention and a method of using the compounds in the treatment of depression and fatigue.

Method of using [1,2,4]triazolo[4,3-a]quinoxaline-4-amine derivatives as antidepressant and antifatigue agents

A series of novel [1,2,4]triazolo[4,3-a]quinoxaline-4-amine derivatives wherein the amine group is optionally substituted with lower alkyl, phenylalkyl having up to three carbon atoms in the alkyl moiety or alkanoyl having from two to five carbon atoms, or the amine group alternatively completes a piperazino ring, the quinoxaline ring is optionally substituted with fluorine, chlorine, bromine or methoxy, and the triazolo ring is optionally substituted with lower alkyl, lower perfluoroalkyl or phenyl are disclosed. These novel compounds are useful for treatment of symptoms associated with depression. Also disclosed are pharmaceutical compositions containing the novel compounds of this invention and a method of using the compounds in the treatment of depression and fatigue.

INVESTIGATION OF THE DECOMPOSITION OF 1,3-DIARYL-5-(3-CHLORO-2-QUINOXALYL)-FORMAZANS BY PMR AND MASS SPECTROMETRY

In contrast to triarylformazans, 1,3-diaryl-5-(3-chloro-2-quinoxalyl)formazans are unstable in ordinary organic solvents.When they are heated in chloroform, they undergo acidic cleavage, which leads to the formation of 3-chloro-2-quinoxalylhydrazones of p-substituted benzaldehydes and arenediazonium cations.These compounds, as a result of a redox reaction with the participation of the solvent, are converted to 4-chloro-1-(4-Y-phenyl)-1,2,4-triazoloquinoxalines, substituted benzenes, nitrogen, and hydrogen chloride.The formation of the latter transforms the entire decomposition process into an autocatalytic process.Effects of chemical polarization of the nuclei (CPN), which unambiguously indicate the intermediate formation of diazoaryl radicals during the process, are observed in the PMR spectra of the final products.Such CPN effects, which were also observed in dimethyl sulfoxide (DMSO) and glacial acetic acid, indicate a process involving the oxidative formation of annelated triazoles from α-azahetarylhydrazones via a radical pathway within a solvent "cage."