32601-86-8

Usage

Chemical Properties

Pink solid

InChI:InChI=1/C9H7ClN2/c1-6-9(10)12-8-5-3-2-4-7(8)11-6/h2-5H,1H3

Upstream product

• 14003-34-0 3-methylquinoxalin-2-ol 
• 95-54-5 1,2-diamino-benzene 
• 583-63-1 ortoquinone 
• 1448-87-9 2-chloroquinoxaline 
• 25554-84-1 2-(ethoxycarbonothioylthio)acetic acid 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 14003-34-0 3-methyl-2-oxo-1,2-dihydroquinoxaline 

Downstream Products

• 3149-26-6 2-methoxy-3-methylquinoxaline 
• 5433-92-1 sulfanilic acid-(3-methyl-quinoxalin-2-ylamide) 
• 58773-29-8 3-methyl-1,2-dihydroquinoxaline-2-thione 
• 7251-61-8 2-methylquinoxaline 
• 51144-19-5 (3-methyl-quinoxalin-2-yl)-hydrazine 
• 6640-55-7 2-methyl-1,2,3,4-tetrahydroquinoxaline 
• 6307-63-7 3-Morpholino-2-methyl-chinoxalin 
• 113477-56-8 2-(2-propynyl)-3-methylquinoxaline 
• 113477-55-7 2-allenyl-3-methyl-quinoxaline 
• 6323-89-3 1-Phenyl-2(3-oxo-4H-chinoxal-2-yl)ethen 
• 75163-24-5 2-Methyl-3-phenylethynyl-quinoxaline 
• 67570-84-7 3-methyl-N-phenylquinoxalin-2-amine 
• 60638-86-0 2-methyl-3-phenylsulphonylquinoxaline 
• 111339-51-6 2-methyl-3-(phenylthio)quinoxaline 

Relevant academic research and scientific papers

Synthesis and reactivity of pyrrolo[1,2-a]quinoxalines. Crystal structure and AM1 calculation

2-Methylquinoxaline reacts with ethyl bromopyruvate giving 2-substituted pyrrolo[1,2-a]quinoxalines. The yield of the condensation depends on the functionalization of starting materials, and optimization is obtained with 2-dimethylamino-3-methylquinoxalin

Antiplasmodial 2-thiophenoxy-3-trichloromethyl quinoxalines target the apicoplast of Plasmodium falciparum

The identification of a plant-like Achille's Heel relict, i.e. the apicoplast, that is essential for Plasmodium spp., the causative agent of malaria lead to an attractive drug target for new antimalarials with original mechanism of action. Although it is not photosynthetic, the apicoplast retains several anabolic pathways that are indispensable for the parasite. Based on previously identified antiplasmodial hit-molecules belonging to the 2-trichloromethylquinazoline and 3-trichloromethylquinoxaline series, we report herein an antiplasmodial Structure-Activity Relationships (SAR) study at position two of the quinoxaline ring of 16 newly synthesized compounds. Evaluation of their activity toward the multi-resistant K1 Plasmodium falciparum strain and cytotoxicity on the human hepatocyte HepG2 cell line revealed a hit compound (3k) with a PfK1 EC50 value of 0.3 μM and a HepG2 CC50 value of 56.0 μM (selectivity index = 175). Moreover, hit-compound 3k was not cytotoxic on VERO or CHO cell lines and was not genotoxic in the in vitro comet assay. Activity cliffs were observed when the trichloromethyl group was replaced by CH3, CF3 or H, showing that this group played a key role in the antiplasmodial activity. Biological investigations performed to determine the target and mechanism of action of the compound 3k strongly suggest that the apicoplast is the putative target as showed by severe alteration of apicoplaste biogenesis and delayed death response. Considering that there are very few molecules that affect the Plasmodium apicoplast, our work provides, for the first time, evidence of the biological target of trichloromethylated derivatives.

Synthesis, crystal structure and calculation of oxides of 2-methylamino-3-methyl quinoxaline

Monoxide and dioxide of animo quinoxaline were synthesized and characterized by 1H NMR, 13C NMR and HRMS. The result shows that monoxide is main product. 1H NMR analysis, quantum calculation and crystal structure all indicate that the monoxide is 4-oxide structure but not 1-oxide structure. The subsequent discussions of electronic effect and steric effect of 1-oxide and 4-oxide support the conclusion that 4-oxide is dominant product, which is consistent with 1H NMR analysis and crystal structure. At last, the calculated structure is in good agreement with the crystal structure in this paper, which indicates that the calculation result in this paper is credible.

Design and synthesis of new quinoxaline derivatives as anticancer agents and apoptotic inducers

The quinoxaline scaffold is a promising platform for the discovery of active chemotherapeutic agents. Three series of quinoxaline derivatives were synthesized and biologically evaluated against three tumor cell lines (HCT116 human colon carcinoma, HepG2, liver hepatocellular carcinoma and MCF-7, human breast adenocarcinoma cell line), in addition to VEGFR-2 enzyme inhibition activity. Compounds VIId, VIIIa, VIIIc, VIIIe and XVa exhibited promising activity against the tested cell lines and weak activity against VEGFR-2. Compound VIIIc induced a significant disruption in the cell cycle profile and cell cycle arrest at the G2/M phase boundary. In further assays, the cytotoxic effect of the highly active compounds was determined using a normal Caucasian fibroblast-like fetal lung cell line (WI-38). Compound VIIIc could be considered as a lead compound that merits further optimization and development as an anti-cancer and an apoptotic inducing candidate against the HCT116 cell line.

Method for preparing ethylene glycol compounds

The invention provides a method for preparing ethylene glycol compounds. The preparation method is short in route, the yield is high, and the operation is simple, Compounds VIII and IX serve as intermediates for preparing the ethylene glycol compounds in the invention, and the ethylene glycol compounds disclosed by the invention are prepared by taking the compounds VIII and IX as the intermediates. The method is high in yield, high in purity and suitable for industrial production.

DNA topoisomerase II inhibition has the activity of modulating kui analogue and its preparation method and application

The invention discloses a quinoxalinone analog with DNA (deoxyribonucleic acid) topoismerase II inhibiting activity, an optical isomer, diastereoisomer or racemic mixture, or pharmaceutically acceptable salt, solvate, prodrug, intermediate or metabolite thereof. The structural general formula is disclosed as Formula (I), wherein R1, R2, R3, R4, R5 and Ar are defined in the specification. The invention also discloses a preparation method of the compounds and application of the compounds as drugs and in treating tumors. The compounds have the advantages of definite curative effect and small toxic and side effects, enriches the varieties of inhibitors of drugs for treating diseases caused by topoismerase II expression abnormity in the prior art, and is hopeful to become clinical drugs with higher therapeutic index.

Inexpensive Radical Methylation and Related Alkylations of Heteroarenes

A simple method for the introduction of a methyl and higher aliphatic group to various heteroarenes using very inexpensive reagents is described. It is based on the radical addition of a carboxylic xanthate followed by decarboxylation. Depending on the heteroarene structure, the decarboxylation can be spontaneous or induced by heating in N,N-dimethylacetamide or N-methyl pyrrolidone in a microwave oven.

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.

A novel method for heterocyclic amide-thioamide transformations

In this paper, we introduce a novel and convenient method for the transformation of heterocyclic amides into heteocyclic thioamides. A two-step approach was applied for this transformation: Firstly, we applied a chlorination of the heterocyclic amides to afford the corresponding chloroheterocycles. Secondly, the chloroherocycles and N-cyclohexyl dithiocarbamate cyclohexylammonium salt were heated in chloroform for 12 h at 61°C to afford heteocyclic thioamides in excellent yields.

Design, synthesis, biological evaluation and molecular docking study on peptidomimetic analogues of XK469

XK469 is identified as a potent quinoxaline antineoplastic agent based on its significant clinical efficacy. It probably exerts its activity via DNA topoisomerase II (topo II) inhibition. To obtain more effective antineoplastic agents, a spectrum of peptidomimetic-type quinoxaline analogues of XK469 was herein designed, synthesized, and evaluated. Few compounds (e.g. 13a and 13b) exhibited obvious cytotoxicity indicated by in?vitro anti-proliferative assay. SAR investigation revealed that introducing of hydrophobic tert-butylamine or dodecylamine moiety at the 3-position of quinoxaline core is favorable for achieving a better anti-proliferative potency, while peptidomimetic derivatives only yielded moderate cytotoxicity. Compounds with improved anti-proliferative activities also demonstrated decent anti-metastatic potencies comparable with that of doxorubicin (Doxo) based on in?vivo mouse model study. The topo II-mediated kinetoplast DNA (kDNA) decatenation assay as well as molecular docking studies implicated that these compounds tend to be potent topo II inhibitors. Overall, compounds 13a and 13b, 13b in particular, standed out from various assessments and might be promising candidates for further chemical optimization.