6,7-Dimethoxy-2-phenylquinoxaline

Base Information

• Chemical Name: 6,7-Dimethoxy-2-phenylquinoxaline
• CAS No.: 146535-11-7
• Molecular Formula: C16H14 N2 O2
• Molecular Weight: 266.299
• DSSTox Substance ID: DTXSID70163393
• Nikkaji Number: J623.662F
• Wikidata: Q27074335
• NCI Thesaurus Code: C1731
• ChEMBL ID: CHEMBL71191
• Mol file: 146535-11-7.mol

Synonyms:6,7-dimethoxy-3-phenylquinoxaline;AG-1296;AG1296;tyrphostin AG 1296;tyrphostin-AG1296

Chemical Property of 6,7-Dimethoxy-2-phenylquinoxaline

Chemical Property:

• Vapor Pressure: 6.97E-07mmHg at 25°C
• Boiling Point: 420.2°Cat760mmHg
• PKA: 0.48±0.30(Predicted)
• Flash Point: 151.8°C
• PSA: 44.24000
• Density: 1.192g/cm³
• LogP: 3.31400
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: Soluble in DMSO.
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 266.105527694
• Heavy Atom Count: 20
• Complexity: 307

Purity/Quality:

99.3% ^*data from raw suppliers

Tyrphostin AG-1296 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)N=CC(=N2)C3=CC=CC=C3)OC
• Description: Protein tyrosine kinase (PTK) inhibitors are potential antiproliferative agents for diseases caused by the hyperactivity of PTKs. Tyrphostins are a class of antiproliferative compounds which act as PTK blockers. PTK inhibitors specific for platelet-derived growth factor (PDGF) receptor kinase could help in the treatment of atherosclerosis, restenosis, pulmonary fibrosis, and gliomas. AG-1296 is a potent and selective inhibitor of PDGF receptor kinase with an IC50 value of about 0.4 μM both in vitro and in cells (Swiss 3T3 cells). It inhibits ligand-stimulated DNA synthesis in platelet-derived growth factor receptor and stem cell factor/kit receptor transfected cells with an IC50 values of 1.5 and 1.8 μM, respectively. Treatment of sis oncogene transfected NIH3T3 cells with AG-1296 reverses the transformed phenotype.
• Uses: Tyrphostin AG 1296, is the platelet-derived growth factor receptor (PDGFR) inhibitor, which can causes growth inhibition in glioblastoma cells.

Technology Process of 6,7-Dimethoxy-2-phenylquinoxaline

There total 12 articles about 6,7-Dimethoxy-2-phenylquinoxaline 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: 90.0%

phenethylamine (64-04-0) + 4,5-dimethoxybenzene-1,2-diamine (27841-33-4) → 6,7-dimethoxy-3-phenylquinoxaline (146535-11-7)

Guidance literature:

With oxygen; copper(I) bromide; In chlorobenzene; at 20 ℃; for 5h;

DOI:10.1039/c7ob00122c

Reference yield: 88.0%

phenylethane 1,2-diol (93-56-1) + 4,5-dimethoxybenzene-1,2-diamine (27841-33-4) → 6,7-dimethoxy-3-phenylquinoxaline (146535-11-7)

Guidance literature:

With C₁₈H₂₄ClIrN₃O⁽¹⁺⁾*Cl^(1-); potassium hydroxide; In water; for 24h; Schlenk technique; Reflux; Green chemistry;

DOI:10.1039/c8gc03744b

Reference yield: 80.0%

N-{2-[(2-bromo-4,5-dimethoxyphenyl)amino]-2-phenylethyl}-4-methylbenzenesulfonamide → 6,7-dimethoxy-3-phenylquinoxaline (146535-11-7)

Guidance literature:

With copper(l) iodide; sodium hydride; L-proline; In N,N-dimethyl-formamide; at 130 ℃; for 12h; Inert atmosphere;

DOI:10.1002/ejoc.201700506

upstream raw materials:

phenylglyoxal hydrate

4,5-dimethoxybenzene-1,2-diamine

4,5-dimethoxy-1,2-dinitrobenzene

1-phenyl-2-hydroxyethanone

Downstream raw materials:

6,7-dimethoxy-3-phenylquinoxalin-2(1H)-one

Refernces

• 1、 Chakrabarti, Kaushik,Maji, Milan,Kundu, Sabuj. "Cooperative iridium complex-catalyzed synthesis of quinoxalines, benzimidazoles and quinazolines in water". supporting information. p. 1999 - 2004. Retrieved 2019/04/27.
• 2、 Gopalaiah, Kovuru,Saini, Anupama,Chandrudu, Sankala Naga,Rao, Devarapalli Chenna,Yadav, Harsh,Kumar, Binay. "Copper-catalyzed aerobic oxidative coupling of o-phenylenediamines with 2-aryl/heteroarylethylamines: direct access to construct quinoxalines". . p. 2259 - 2268. Retrieved 2017/03/20.