6307-64-8

Usage

Heterocyclic organic compound

The compound contains a quinoxaline ring and two morpholine groups, making it a complex organic molecule with potential applications in various fields.

Quinoxaline ring

A heterocyclic aromatic ring system consisting of two fused six-membered rings with one nitrogen atom in each ring, contributing to the compound's chemical properties and potential applications.

Morpholine groups

Two morpholine groups (a five-membered heterocyclic ring with one oxygen and four carbon atoms) are attached to the 2 and 3 positions of the quinoxaline ring, contributing to the compound's unique properties.

Potential applications

2,3-di(morpholin-4-yl)quinoxaline has been studied for its potential applications in medicinal chemistry and material science, making it a versatile compound.

Biological activities

The compound exhibits promising biological activities, such as anticancer, antitubercular, and antiprotozoal properties, making it a potential candidate for drug development.

Building block for synthesis

Due to its unique structural features, 2,3-di(morpholin-4-yl)quinoxaline is a valuable building block for the synthesis of complex organic molecules and functional materials, contributing to its potential applications in the materials industry.

Upstream product

• 2213-63-0 2,3-dichloroquinoxaline 
• 110-91-8 morpholine 
• 23719-78-0 2,3-dibromo-quinoxaline 
• 75163-15-4 2-chloro-3-(phenylethynyl)quinoxaline 

Relevant academic research and scientific papers

Activities of quinoxaline, nitroquinoxaline, and [1,2,4]triazolo [4,3-a]quinoxaline analogs of mmv007204 against schistosoma mansoni

The reliance on one drug, praziquantel, to treat the parasitic disease schistosomiasis in millions of people a year shows the need to further develop a pipeline of new drugs to treat this disease. Recently, an antimalarial quinoxaline derivative (MMV007204) from the Medicines for Malaria Venture (MMV) Malaria Box demonstrated promise against Schistosoma mansoni. In this study, 47 synthesized compounds containing quinoxaline moieties were first assayed against the larval stage of this parasite, newly transformed schistosomula (NTS); of these, 16 killed over 70% NTS at 10mM. Further testing against NTS and adult S. mansoni yielded three compounds with 50% inhibitory concentrations (IC50s) of#0.31mM against adult S. mansoni and selectivity indices of$8.9. Administration of these compounds as a single oral dose of 400mg/kg of body weight to S. mansoni-infected mice yielded only moderate worm burden reduction (WBR) (9.3% to 46.3%). The discrepancy between these compounds' good in vitro activities and their poor in vivo activities indicates that optimization of their pharmacokinetic properties may yield compounds with greater bioavailabilities and better antischistosomiasis activities in vivo.

Difuran-substituted quinoxalines as a novel class of PI3Kα H1047R mutant inhibitors: Synthesis, biological evaluation and structure-activity relationship

Phosphatidylinositol 3-kinase α (PI3Kα) is the most frequently mutated kinase in human cancers, making it an attractive therapeutic target for cancer treatment. We identified a structurally novel PI3Kα H1047R mutant inhibitor Hit-01 (EC50 = 76.0 μM) through a high-throughput screening campaign. Chemical optimizations enabled us to discover compound 7b, which strongly inhibited PI3Kα H1047R mutant with an EC50 value of 0.137 μM, over 500-fold more potent than Hit-01. Western blotting analysis suggested that 7b could decrease the phosphorylation level of p-AKT, another proof that 7b inhibited PI3Kα H1047R function. Cell viability assay revealed that 7b inhibited HCT116 cancer cell growth with an IC50 value of 11.23 μM. In addition, 7b was found to arrest cell cycle at G1 phase and induce cell apoptosis via up-regulation of caspase-3, caspase-8 and caspase-9 protein expressions. Collectively, all these data demonstrated that 7b could be a promising lead for the development of structurally novel PI3Kα inhibitors.

Electrochemical reduction of quinoxalinoquinoxaline

The electrochemical reduction of quinoxalinoquinoxaline gives fluoflavine (2) the structure of which is discussed.The electrochemical reduction of fluoflavine in acidic medium leads to a hexahydroquinolinoquinoxaline.A reduction mechanism is proposed based on cyclic voltammetry results and preparative electrolysis.The results obtained in the case of quinoxalinoquinoxaline are used to rationalize the results obtained in the case of pyrazinopyrazines and pyrazinoquinoxalines.

Alkynyl- and Dialkynyl-quinoxalines. Synthesis of Condensed Quinoxalines

Condensation of 2-chloro- and 2,3-dichloroquinoxalines with alk-1-ynes in the presence of bis(triphenylphosphine)palladium(II) dichloride and copper(I) iodide gives mono- and di-alkynylquinoxalines.Addition of amines to these products gives stable enamines; hydration gives 2'-oxoalkyl compounds which exist predominantly in the intramolecularly hydrogen-bonded enol form.Condensation of the alkynylquinoxalines with diethyl sodiomalonate, and related compounds, yields pyridoquinoxalin-4-one derivatives. 2-Alkynyl-3-chloroquinoxalines are intermediates for convenient syntheses of pyrroloquinoxalines.