146535-11-7

Usage

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

Upstream product

• 582-24-1 1-phenyl-2-hydroxyethanone 
• 27841-33-4 4,5-dimethoxybenzene-1,2-diamine 
• 24395-14-0 N-(p-tolylsulfonyl)-2-phenylaziridine 
• 16791-41-6 2-bromo-4,5-dimethoxyaniline 
• 93-56-1 phenylethane 1,2-diol 
• 64-04-0 phenethylamine 
• 3395-03-7 4,5-dimethoxy-1,2-dinitrobenzene 
• 1074-12-0 phenylglyoxal hydrate 

Downstream Products

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

Relevant academic research and scientific papers

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.

Cooperative iridium complex-catalyzed synthesis of quinoxalines, benzimidazoles and quinazolines in water

Herein, an efficient methodology for the synthesis of a diverse class of N-heterocyclic moieties, such as quinoxalines, benzimidazoles and quinazolines, was developed in water using bio-renewable alcohols. The quinoxalines were successfully synthesized from a wide range of diamines and nitroamines with diols in air. Interestingly, benzimidazoles and quinazolines were synthesized with excellent isolated yields without using any external base. Finally, the preparative scale synthesis of various N-heterocycles and pharmaceutically active quinoxalines established the practicability of this protocol. For this iridium system, a metal-ligand cooperative mechanism was proposed based on kinetic and DFT studies.

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.

Accessing Quinoxalines by Ring-Opening/Cyclization/Detosylation/Aromatization of Activated Aziridines with 2-Bromoanilines: Synthesis of Tyrphostin AG 1296

Substituted 2-arylquinoxalines have been synthesized by an unprecedented CuI-catalyzed ring-opening/cyclization reaction followed by detosylation/aromatization of activated aziridines with 2-bromoanilines. The transformation efficiently accommo

Synthesis of 2-arylquinoxalines: Triarylstibane-catalyzed oxidative cyclization of α-hydroxy ketones with 1,2-diamines under aerobic conditions

The reaction of α-hydroxy ketones with 1,2-diamines in the presence of triphenylstibane (10 mol%) as catalyst led to the formation of 2-arylquinoxalines in moderate to good yield under aerobic conditions. This reaction is the first example of oxidative cy

Bis mono- and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase

This invention relates to bis mono- and/or bicyclic aryl and/or heteroaryl compounds exhibiting protein tyrosine kinase inhibition activity. More specifically, it relates to the method of inhibiting abnormal cell proliferation in a patient suffering from a disorder characterized by such proliferation comprising the administration thereto of an EGF and/or PDGF receptor inhibiting effective amount of said bis mono- and/or bicyclic aryl and/or heteroaryl compound and to the preparation of said compounds and their use in pharmaceutical compositions used in this method.

Tyrphostins. 5. Potent inhibitors of platelet-derived growth factor receptor tyrosine kinase: Structure-activity relationships in quinoxalines, quinolines, and indole tyrphostins

A series of 3-indoleacrylonitrile tyrphostins, 2-chloro-3- phenylquinolines, and 3-arylquinoxalines were prepared and tested for inhibition of platelet-derived growth factor receptor tyrosine kinase (PDGF- RTK) activity. The potency of the inhibitors was found to be quinoxalines > quinolines > indoles. Lipophilic groups (methyl, methoxy) in the 6 and 7 positions and phenyl at the 3 position of quinoxalines and quinolines were essential for potency, in contrast to the hydrophilic catechol group in tyrphostins active against EGFR kinase inhibition at different sites. The inhibitors showed selectivity for PDGF and were not active against EGF receptor and HER-2/c-ErbB-2 receptor.