6272-25-9

Usage

InChI:InChI=1/C8H4ClN3O2/c9-8-4-10-7-3-5(12(13)14)1-2-6(7)11-8/h1-4H

Upstream product

• 25652-34-0 2-hydroxy-6-nitroquinoxaline 
• 95-54-5 1,2-diamino-benzene 
• 1196-57-2 quinoxalin-2⁽¹⁾-one 
• 25652-34-0 6-nitroquinoxalin-2(1H)-one 
• 6639-87-8 6-nitroquinoxaline 
• 1196-57-2 2-hydroxyquinoxaline 
• 109541-15-3 6-nitroquinoxaline-N₁-oxide 

Downstream Products

• 115726-26-6 2-amino-6-nitroquinoxaline 
• 142396-51-8 5-amino-2-chloro-6-nitroquinoxaline 
• 1627523-04-9 N-(4-methoxyphenyl)-6-nitroquinoxalin-2-amine 
• 1627523-06-1 2-N-(4-methoxyphenyl)quinoxaline-2,6-diamine 
• 1627523-07-2 2-N-(4-chlorophenyl)quinoxaline-2,6-diamine 
• 1627523-08-3 1-(2-((4-methoxyphenyl)amino)quinoxalin-6-yl)-3-phenylthiourea 
• 1627523-09-4 1-(2-((4-chlorophenyl)amino)quinoxalin-6-yl)-3-phenylurea 
• 1627523-10-7 1-(2-((4-methoxyphenyl)amino)quinoxalin-6-yl)-3-(m-tolyl)urea 
• 1627523-11-8 1-cyclohexyl-3-(2-((4-methoxyphenyl)amino)quinoxalin-6-yl)urea 
• 1627523-12-9 1-(2-((4-chlorophenyl)amino)quinoxalin-6-yl)-3-cyclohexylurea 
• 1627523-13-0 N-(2-((4-methoxyphenyl)amino)quinoxalin-6-yl)benzenesulfonamide 
• 1627523-14-1 N-(2-((4-methoxyphenyl)amino)quinoxalin-6-yl)-4-methylbenzenesulfonamide 
• 1627523-15-2 N-(2-((4-chlorophenyl)amino)quinoxalin-6-yl)-4-methylbenzenesulfonamide 
• 1627523-16-3 N-(2-((4-chlorophenyl)amino)quinoxalin-6-yl)acetamide 

Relevant academic research and scientific papers

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

Design, synthesis and biological evaluation of type-II VEGFR-2 inhibitors based on quinoxaline scaffold

In an effort to develop ATP-competitive VEGFR-2 selective inhibitors, a series of new quinoxaline-based derivatives was designed and synthesized. The target compounds were biologically evaluated for their inhibitory activity against VEGFR-2. The design of the target compounds was accomplished after a profound study of the structure activity relationship (SAR) of type-II VEGFR-2 inhibitors. Among the synthesized compounds, 1-(2-((4-methoxyphenyl)amino)-3- oxo-3,4 dihydroquinoxalin-6-yl)-3-phenylurea (VIIa) displayed the highest inhibitory activity against VEGFR-2. Molecular modeling study involving molecular docking and field alignment was implemented to interpret the variable inhibitory activity of the newly synthesized compounds.

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.

Bicyclic aromatic substituted pyridone derivative

Disclosed is a compound represented by the formula (I): Wherein R1 and R2 independently represent a hydrogen atom, a lower alkyl group or the like; X1, X2 and X3 independently represent a methine group or a nitrogen atom; Y1 and Y3 independently represent a single bond, —O— or the like; Y2 represents a lower alkylene group or the like; W1 to W4 independently represent a single bond, a methylene group or the like; L represents a single bond, a methylene group or the like; Z1 and Z2 independently represent a single bond, a C1-4 alkylene group or the like; Ar1 represents an aromatic carbocyclic ring or the like; and Ar2 represents a bicyclic aromatic carbocyclic ring or the like. The compound is useful as a pharmaceutical for a central disease, a cardiovascular disease or a metabolic disease.

BICYCLIC AROMATIC SUBSTITUTED PYRIDONE DERIVATIVE

Disclosed is a compound represented by the formula (I): wherein R1 and R2 independently represent a hydrogen atom, a lower alkyl group or the like; X1, X2 and X3 independently represent a methine group or a nitrogen atom; Y1 and Y3 independently represent a single bond, -O- or the like; Y2 represents a lower alkylene group or the like; W1 to W4 independently represent a single bond, a methlene group or the like; L represents a single bond, a methylene group or the like; Z1 and Z2 independently represent a single bond, a C1-4 alkylene group or the like; Ar1 represents an aromatic carbocyclic ring or the like; and Ar2 represents a bicyclic aromatic carbocyclic ring or the like. The compound is useful as a pharmaceutical for a central disease, a cardiovascular disease or a metabolic disease.

Quinazoline and benzimidazole MCH-1R antagonists

We have modified the previously reported 2-aminoquinoline 1 to provide two novel series of MCH-1R antagonists. Representative compounds from the quinazoline and benzimidazole series have been shown to be potent and selective, with promising in vitro eADME profiles.

NIACIN RECEPTOR AGONISTS, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF TREATMENT

Compounds of the formula (I): as well as pharmaceutically acceptable salts and solvates are disclosed. The compounds are useful for treating dyslipidemias, and in particular, reducing serum LDL, VLDL and triglycerides, and raising HDL levels. Pharmaceutic

Synthesis and excitatory amino acid pharmacology of a series of heterocyclic-fused quinoxalinones and quinazolinones

As part of our program aimed at the development of potent excitatory amino acid antagonists, we synthesized and evaluated a series of substituted 1,2,4- triazolo[4,3-a]quinoxalin-4(5H)-ones, 4, tetrazolo[1,5-a]quinoxalin-4(5H)- ones, 5, and pyrazolo[1,5-c]quinazolin-5(6H)-ones, 6, and an imidazo[1,2- a]quinoxalin-4(5H)-one, 7. In general, the same heterocycles which demonstrated the best affinity for the AMPA receptor also demonstrated the best affinity for the glycine site on the NMDA receptor complex. 1-Propyl- 7,8-dichloro-1,2,4-triazolo[4,3-a]quinoxalin-4(5H)-one, 4d, was found to bind with the greatest affinity to the AMPA receptor with an IC50 of 0.83 μM and antagonized 40 μM AMPA-induced depolarization in the cortical slice preparation with an IC50 of 44 μM. 7,8-Dichloro-1,2,4-triazolo[4,3- a]quinoxalin-4(5H)-one, 4a, and 7,8-dichloroimidazo[1,2-a]quinoxalin-4(5H)- one, 7, possessed the best affinity for the glycine site with IC50 values of 0.63 and 1.26 μM, respectively. It is noteworthy that the SAR for the heterocyclic compounds did not directly parallel that of known quinoxalinediones (e.g. DNQX, 2, and DCQX, 15) at the AMPA receptor nor that of the kynurenic acids at the glycine site on the NMDA receptor complex.

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.