146535-11-7

Basic information

• Product Name: TYRPHOSTIN AG 1296
• Synonyms: TYRPHOSTIN AG 1296;AG 1296;6,7-DIMETHOXY-2-PHENYLQUINOXALINE;6,7-DIMETHOXY-3-PHENYLQUINOXALINE;Quinoxaline,6,7-dimethoxy-2-phenyl-
• CAS NO: 146535-11-7
• Molecular Formula: C₁₆H₁₄N₂O₂
• Molecular Weight: 266.29
• Product Categories: Inhibitors
• Mol File: 146535-11-7.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 420.2°Cat760mmHg
• Flash Point: 151.8°C
• Appearance: /
• Density: 1.192g/cm³
• Vapor Pressure: 6.97E-07mmHg at 25°C
• Refractive Index: 1.617
• Storage Temp.: 2-8°C
• Solubility: Soluble in DMSO.
• PKA: 0.48±0.30(Predicted)
• Sensitive: Light Sensitive
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: TYRPHOSTIN AG 1296(CAS DataBase Reference)
• NIST Chemistry Reference: TYRPHOSTIN AG 1296(146535-11-7)
• EPA Substance Registry System: TYRPHOSTIN AG 1296(146535-11-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 146535-11-7(Hazardous Substances Data)

Usage

Description

TYRPHOSTIN AG 1296 is a potent and selective inhibitor of the platelet-derived growth factor receptor (PDGFR), belonging to the class of antiproliferative compounds known as Tyrphostins. These compounds act as protein tyrosine kinase (PTK) blockers, which are potential antiproliferative agents for diseases caused by the hyperactivity of PTKs. AG-1296 has demonstrated the ability to inhibit ligand-stimulated DNA synthesis in PDGFR and stem cell factor/kit receptor transfected cells, as well as reverse the transformed phenotype in sis oncogene transfected NIH3T3 cells.

Uses

Used in Pharmaceutical Industry:
TYRPHOSTIN AG 1296 is used as an antiproliferative agent for the treatment of diseases caused by the hyperactivity of protein tyrosine kinases (PTKs). Its primary application is as a PDGFR inhibitor, which can cause growth inhibition in glioblastoma cells, making it a potential therapeutic option for cancer treatment.
Used in Cardiovascular Applications:
TYRPHOSTIN AG 1296 is used as a therapeutic agent for atherosclerosis, restenosis, and other cardiovascular diseases. As a PDGFR inhibitor, it can help in the treatment of these conditions by targeting the hyperactivity of PTKs involved in the development and progression of these diseases.
Used in Pulmonary Applications:
TYRPHOSTIN AG 1296 is used as a treatment option for pulmonary fibrosis, a lung disease characterized by the thickening and scarring of lung tissue. By inhibiting the PDGFR, AG-1296 can potentially slow down or prevent the progression of this disease.
Used in Cancer Research:
TYRPHOSTIN AG 1296 is used as a research tool in the study of cancer cell growth and proliferation. Its ability to inhibit PDGFR makes it a valuable compound for investigating the role of this receptor in cancer development and for identifying potential therapeutic targets in various types of cancer.

References

1) Kovalenko et al. (1997), Phosphorylation site-specific inhibition of platelet-derived growth factor beta-receptor autophosphorylation by the receptor blocking tyrphostin AG1296; Biochemistry, 36 6260 2) Krystal et al. (1997), Induction of apoptosis and inhibition of small cell lung cancer growth by the quinoxaline tyrphostins; Cancer Res., 57 220 3) Strutz et al. (2001), TGF-beta 1 induces proliferation in human renal fibroblasts via induction of basic fibroblast growth factor (FGF-2); Kidney Int., 59 579

InChI:InChI=1/C16H14N2O2/c1-19-15-8-12-13(9-16(15)20-2)18-14(10-17-12)11-6-4-3-5-7-11/h3-10H,1-2H3

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Downstream Products

• 50616-92-7 6,7-dimethoxy-3-phenylquinoxalin-2(1H)-one 

Relevant articles and documents

Nickel-Catalyzed Direct Synthesis of Quinoxalines from 2-Nitroanilines and Vicinal Diols: Identifying Nature of the Active Catalyst

The inexpensive and simple NiBr2/1,10-phenanthroline system-catalyzed synthesis of a series of quinoxalines from both 2-nitroanilines and 1,2-diamines is demonstrated. The reusability test for this system was performed up to the seventh cycle, which afforded good yields of the desired product without losing its reactivity significantly. Notably, during the catalytic reaction, the formation of the heterogeneous Ni-particle was observed, which was characterized by PXRD, XPS, and TEM techniques.

Platelet-derived growth factor receptor inhibitor AG1296 preparation method (by machine translation)

The invention discloses a platelet-derived growth factor receptor inhibitor AG1296 preparation method, in order to 3 - (3, 4 - dimethyl practiced amino) - 3 - phenyl - acrylate as raw materials synthesis. The invention can greatly reduce the AG1296 synthesis cost, has wide application. (by machine translation)

Copper-catalyzed aerobic oxidative coupling of o-phenylenediamines with 2-aryl/heteroarylethylamines: direct access to construct quinoxalines

A copper-catalyzed oxidative coupling reaction of o-phenylenediamines with 2-aryl/heteroarylethylamines using molecular oxygen as an oxidant has been developed. This approach provides a practical and direct access to construct quinoxalines in excellent yields at room temperature. The reaction has a broad substrate scope and exhibits excellent functional-group tolerance. This method could be easily scaled up and applied to the synthesis of biologically active molecules bearing a quinoxaline structural scaffold.