531-46-4

Basic information

• Product Name: 5,12-dihydroquinoxalino[2,3-b]quinoxaline
• Synonyms: 5,12-dihydroquinoxalino[2,3-b]quinoxaline;Fluoflavine;ML-090;6,11-dihydroquinoxalino[2,3-b]quinoxaline
• CAS NO: 531-46-4
• Molecular Formula: C₁₄H₁₀N₄
• Molecular Weight: 234.26
• Mol File: 531-46-4.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly, Heated, Sonicated)
• CAS DataBase Reference: 5,12-dihydroquinoxalino[2,3-b]quinoxaline(CAS DataBase Reference)
• NIST Chemistry Reference: 5,12-dihydroquinoxalino[2,3-b]quinoxaline(531-46-4)
• EPA Substance Registry System: 5,12-dihydroquinoxalino[2,3-b]quinoxaline(531-46-4)

Safety Data

• Hazardous Substances Data: 531-46-4(Hazardous Substances Data)

Usage

Description

NADPH oxidase 1 (NOX1) generates reactive oxygen species (ROS) in colon epithelial cells that interacts with both pathogenic and normal bacteria. Excess ROS production, however, is associated with damage to the intestinal mucosa, inflammatory bowel disease, and prostate cancer. ML-090 is the first identified NOX1-specific inhibitor (IC50 = 360 nM in HEK293 cells) based on a quinoxaline scaffold that demonstrates potent selectivity over NOX2, NOX3, and NOX4 (IC50s ≥ 10 μM) and xanthine oxidase (IC50 = 3.5 μM).

Uses

5,12-Dihydroquinoxalino[2,3-b]quinoxaline is an inhibitor of?NADPH oxidase 1 (NOX1).

Upstream product

• 6640-47-7 2,3-diaminoquinoxaline 
• 95-54-5 1,2-diamino-benzene 
• 2213-63-0 2,3-dichloroquinoxaline 
• 144-62-7 oxalic acid 
• 15804-19-0 quinoxaline-2,3-dione 
• 124831-91-0 3-(α-chlorobenzyl)-1,2-dihydroxyquinoxalin-2-one 
• 471-46-5 Oxalamide 
• 64-17-5 ethanol 
• 102880-02-4 1,2-dibutoxy-tetrachloro-ethane 
• 166271-34-7 N-(3-chloroquinoxalin-2-yl)-benzenesulfonamide 
• 258-14-0 Chinoxalino<2,3-b>chinoxalin 

Downstream Products

• 258-14-0 Chinoxalino<2,3-b>chinoxalin 
• 91362-51-5 N-(1H-Benzoimidazol-2-ylmethyl)-benzene-1,2-diamine 

Relevant articles and documents

Cyclodehydration of 3-[α-(2′-aminophenylamino)- benzylidene]-2-oxo-1,4-dihydroquinoxaline into 2,2′-bisbenzimidazole with elimination of the benzylidene fragment [5]

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The use of diethylene glycol in the synthesis of 2,2'-bibenzimidazole from o-phenylenediamine and oxalic acid

One- and two-step syntheses of 2,2'-bibenzimidazole were compared. Diethylene glycol was used as solvent that provides good solubility of the substrates. The limitation of the one-step preparation is the formation of the by-product, fluoflavine. The two-step synthesis proceeds with the separation of the intermediate product, 1,4-dihydroquinoxaline-2,3-dione, and the final product is only 2,2'-bibenzimidazole. The total yield of the two-step synthesis is above 85%.

Efficient synthesis and characterization of novel bibenzimidazole oligomers and polymers as potential conjugated chelating ligands

A simple and mild condensation route for the synthesis of novel bibenzimidazole oligomers and polymers is reported here using methyl 2,2,2-trichloroacetimidate as a key starting material. The dimer, trimer, tetramer, and polymers of bibenzimidazole were synthesized as a new series of potential conjugated chelating ligands for metallopolymer studies. The polymers show a maximum absorption at around 400 nm. The optical band gap of the polymer was estimated to be 2.68 eV.