5,12-dihydroquinoxalino[2,3-b]quinoxaline

Base Information

• Chemical Name: 5,12-dihydroquinoxalino[2,3-b]quinoxaline
• CAS No.: 531-46-4
• Molecular Formula: C14H10N4
• Molecular Weight: 234.26
• Hs Code.: 2933990090
• Mol file: 531-46-4.mol

Synonyms:5,11-dihydro-5,6,11,12-tetraazanaphthacene;

Chemical Property of 5,12-dihydroquinoxalino[2,3-b]quinoxaline

Chemical Property:

• Melting Point: >262°C (dec.)
• PSA: 57.36000
• LogP: 3.15460
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly, Heated, Sonicated)

Purity/Quality:

98%min ^*data from raw suppliers

5,12-Dihydroquinoxalino[2,3-b]quinoxaline(~90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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).

Technology Process of 5,12-dihydroquinoxalino[2,3-b]quinoxaline

There total 18 articles about 5,12-dihydroquinoxalino[2,3-b]quinoxaline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2,3-dichloroquinoxaline (2213-63-0) + 1,2-diamino-benzene (95-54-5) → 5,12-dihydroquinoxalino[2,3-b]quinoxaline (531-46-4,55977-58-7)

Guidance literature:

In N,N-dimethyl-formamide; for 1h; Reflux;

DOI:10.1515/znb-2012-0411

Reference yield: 96.0%

1,2-diamino-benzene (95-54-5) + N-(3-chloroquinoxalin-2-yl)-benzenesulfonamide (166271-34-7) → 5,12-dihydroquinoxalino[2,3-b]quinoxaline (531-46-4,55977-58-7)

Guidance literature:

In N,N-dimethyl-formamide; for 0.25h; Heating;

DOI:10.1007/BF01165702

Reference yield: 96.0%

quinoxaline-2,3-dione (15804-19-0,6287-20-3) + 1,2-diamino-benzene (95-54-5) → 5,12-dihydroquinoxalino[2,3-b]quinoxaline (531-46-4,55977-58-7) + 2,2'-bi-1H-benzimidazole (6965-02-2)

Guidance literature:

at 240 ℃; for 1h; Further Variations:; Temperatures; Reaction partners; Product distribution; solid-state reaction;

DOI:10.1002/1099-0690(200204)2002:8<1368::AID-EJOC1368>3.0.CO;2-6

upstream raw materials:

2,3-diaminoquinoxaline

1,2-diamino-benzene

2,3-dichloroquinoxaline

quinoxaline-2,3-dione

Downstream raw materials:

Chinoxalino<2,3-b>chinoxalin

N-(1H-Benzoimidazol-2-ylmethyl)-benzene-1,2-diamine

Refernces

• 1、 Pressler, Jens,Beckert, Rainer,Rau, Sven,Menzel, Roberto,Birckner, Eckhard,Guenther, Wolfgang,Goerls, Helmar. "A surprising formation of novel bridged bis-benzimidazoles by oxidation of diaminoquinoxalines". . p. 367 - 372. Retrieved 2012.
• 2、 Isoda, Kyosuke,Nakamura, Masaharu,Tatenuma, Toshinori,Ogata, Hironori,Sugaya, Tomoaki,Tadokoro, Makoto. "Synthesis and characterization of electron-accepting nonsubstituted tetraazaacene derivatives". supporting information. p. 937 - 939. Retrieved 2012/11/13.