55686-94-7

Usage

Uses

Used in Pharmaceutical Research:
2-Chloro-7-nitroquinoxaline is used as a reagent in pharmaceutical research for its potential as an antiviral agent, specifically against HIV. Its antiviral activity is attributed to its ability to inhibit viral replication and reduce the spread of the virus.
Used in Organic Synthesis:
In the field of organic synthesis, 2-chloro-7-nitroquinoxaline is employed as a key intermediate in the synthesis of various organic compounds, contributing to the development of new pharmaceuticals and chemical products.
Used in Neuroscience Research:
2-Chloro-7-nitroquinoxaline is used as a fluorescent probe in neuroscience research, enabling the study of ion channels and synaptic transmission. Its fluorescent properties allow for the visualization and analysis of these biological processes, providing valuable insights into their function and potential therapeutic targets.
Used in Neuroprotection and Glutamate Receptor Modulation:
2-CHLORO-7-NITROQUINOXALINE has been investigated for its neuroprotective effects, which involve the protection of neurons from damage or degeneration. Additionally, 2-chloro-7-nitroquinoxaline has demonstrated the ability to modulate glutamate receptors, which play a crucial role in neuronal excitability and synaptic plasticity. These properties make it a promising candidate for the development of treatments for neurological disorders associated with glutamate dysregulation.

Upstream product

• 89898-96-4 7-nitroquinoxaline-2(1H)-one 
• 109541-16-4 7-nitroquinoxaline-N₁-oxide 
• 89898-96-4 2-Hydroxy-7-nitroquinoxaline 
• 6639-87-8 6-nitroquinoxaline 
• 1196-57-2 2-hydroxyquinoxaline 
• 95-54-5 1,2-diamino-benzene 

Downstream Products

• 1261078-70-9 (E)-3-(3-(6-nitroquinoxalin-3-ylamino)phenyl)acrylic acid 
• 1261078-78-7 3-(3-(6-nitroquinoxalin-3-ylamino)phenyl)propanoic acid 
• 1310877-60-1 ethyl 3-(3-(6-nitroquinoxalin-3-ylamino)phenyl)propanoate 
• 1261078-69-6 (E)-ethyl 3-(3-(6-nitroquinoxalin-3-ylamino)phenyl)acrylate 
• 1261078-75-4 5-(6-nitroquinoxalin-3-ylamino)-2-chlorobenzoic acid 
• 1333465-93-2 ethyl 5-(6-nitroquinoxalin-3-ylamino)-2-chlorobenzoate 
• 1261078-77-6 7-nitro-N-phenylquinoxalin-2-amine 
• 1261078-76-5 N-(3-ethoxyphenyl)-7-nitroquinoxalin-2-amine 

Relevant academic research and scientific papers

6-NITRO-2,3-DIPIPERIDINOQUINOXALINE: ITS UNEXPECTED FORMATION FROM 2-CHLORO-7-NITROQUINOXALINE

Excess piperidine and 2-chloro-7-nitroquinoxaline 1 in diethyl ether give large amounts of the unexpected disubstitution product 6-nitro-2,3-di-piperidinoquinoxaline 3.The mechanism of this very unusual nucleophilic substitution of hydrogen is suggested to involve the oxidation of the dipiperidino-dihydroquinoxaline 10 by dissolved oxygen.

Structure activity relationship (SAR) study identifies a quinoxaline urea analog that modulates IKKβ phosphorylation for pancreatic cancer therapy

Genetic models validated Inhibitor of nuclear factor (NF) kappa B kinase beta (IKKβ) as a therapeutic target for KRAS mutation associated pancreatic cancer. Phosphorylation of the activation loop serine residues (S177, S181) in IKKβ

1, 4, 8-Triazaphenanthrene Derivatives For The Treatment Of Neurodegenerative Disorders

The invention relates to compounds of formula (I), particularly for the use thereof as a medicament, especially in the treatment or prevention of neurogenerative disorders. The invention also relates to the methods for producing said compounds, and to the

QUINOXALINE COMPOUNDS AND USES THEREOF

Provided herein are compounds having a structure of formula (I) and methods of using the disclosed compounds to inhibit ΙΚΚβ activity.

Multi-gram preparation of 7-nitroquinoxalin-2-amine

Methodologies to obtain quinoxaline compounds regioselectively are rarely reported in literature, thus regioselective and multi-gram methodologies to obtain these derivatives are desirable to explore the entire potential of these scaffolds for academic and/or commercial application. A facile and multi-gram methodology is described to obtain compound 7-nitroquinoxalin-2-amine using o-phenylenediamine, a cheap and readily available reactant, as starting material in a five-step procedure in good yields and high purity without further purification such as crystallization or column chromatography.

New 6-Aminoquinoxaline Derivatives with Neuroprotective Effect on Dopaminergic Neurons in Cellular and Animal Parkinson Disease Models

Parkinson's disease (PD) is a neurodegenerative disorder of aging characterized by motor symptoms that result from the loss of midbrain dopamine neurons and the disruption of dopamine-mediated neurotransmission. There is currently no curative treatment for this disorder. To discover druggable neuroprotective compounds for dopamine neurons, we have designed and synthesized a second-generation of quinoxaline-derived molecules based on structure-activity relationship studies, which led previously to the discovery of our first neuroprotective brain penetrant hit compound MPAQ (5c). Neuroprotection assessment in PD cellular models of our newly synthesized quinoxaline-derived compounds has led to the selection of a better hit compound, PAQ (4c). Extensive in vitro characterization of 4c showed that its neuroprotective action is partially attributable to the activation of reticulum endoplasmic ryanodine receptor channels. Most interestingly, 4c was able to attenuate neurodegeneration in a mouse model of PD, making this compound an interesting drug candidate for the treatment of this disorder.

Design and synthesis of small molecule RhoA inhibitors: A new promising therapy for cardiovascular diseases?

RhoA is a member of Rho GTPases, a subgroup of the Ras superfamily of small GTP-binding proteins. RhoA, as an important regulator of diverse cellular signaling pathways, plays significant roles in cytoskeletal organization, transcription, and cell-cycle progression. The RhoA/ROCK inhibitors have emerged as a new promising treatment for cardiovascular diseases. However, to date, RhoA inhibitors are macromolecules, and to our knowledge, small molecular-based inhibitors have not been reported. In this study, a series of first-in-class small molecular RhoA inhibitors have been discovered by using structure-based virtual screening in conjunction with chemical synthesis and bioassay. Virtual screening of ～200,000 compounds, followed by SPR-based binding affinity assays resulted in three compounds with binding affinities to RhoA at the micromolar level (compounds 1-3). Compound 1 was selected for further structure modifications in considering binding activity and synthesis ease. Fourty-one new compounds (1, 12a-v, 13a-h, and 14a-j) were designed and synthesized accordingly. It was found that eight (12a, 12j, 14a, 14b, 14d, 14e, 14 g, and 14h) showed high RhoA inhibition activities with IC50 values of 1.24 to 3.00 μM. A pharmacological assay indicated that two compounds (14g and 14 h) demonstrated noticeable vasorelaxation effects against PE-induced contraction in thoracic aorta artery rings and served as good leads for developing more potent cardiovascular agents.

REGIOSELECTIVITY IN THE REACTION OF NITROQUINOXALINE-N-OXIDES WITH PHOSPHORYL CHLORIDE

6-nitro-, 2-methyl-6-nitro- and 2,3-dimethyl-6-nitroquinoxaline have been transformed into their N-oxides by MCPBA in chloroform; the nitro group orients the oxygen atom preferentially to nitrogen atom N1, but the N4:N1 selectivity is diminished in the methylated derivatives.Under the action of POCl3 (the Meisenheimer reaction), the N-oxides of the unmethylated compounds are transformed into chloro-nitroquinoxalines having lost the N-oxide oxygen atom.The orientation of the entering chloride ion is discussed on the basis of electronic effects induced by the N-oxide and nitro groups, and it is suggested that the last step, the elimination of "HPO2Cl2" is a concerted process.