331662-65-8

Basic information

• Product Name: 4-Hydroxy-5,7-dimethoxy-3-quinolinecarbonitrile
• Synonyms: 4-Hydroxy-5,7-dimethoxy-3-quinolinecarbonitrile;3-Quinolinecarbonitrile, 1,4-dihydro-5,7-diMethoxy-4-oxo-;4-Hydroxy-5,7-diMethoxyquinoline-3-carbonitrile
• CAS NO: 331662-65-8
• Molecular Formula: C12H10N2O3
• Molecular Weight: 230.222
• Mol File: 331662-65-8.mol

Chemical Properties

• Boiling Point: 407.026°C at 760 mmHg
• Flash Point: 199.962°C
• Appearance: /
• Density: 1.332g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.603
• CAS DataBase Reference: 4-Hydroxy-5,7-dimethoxy-3-quinolinecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxy-5,7-dimethoxy-3-quinolinecarbonitrile(331662-65-8)
• EPA Substance Registry System: 4-Hydroxy-5,7-dimethoxy-3-quinolinecarbonitrile(331662-65-8)

Safety Data

• Hazardous Substances Data: 331662-65-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H10N2O3/c1-16-8-3-9-11(10(4-8)17-2)12(15)7(5-13)6-14-9/h3-4,6H,1-2H3,(H,14,15)

Upstream product

• 20428-58-4 α-lithioacetonitrile 
• 712307-63-6 ethyl 2-cyano-3-(3,5-dimethoxyphenylamino)acrylate 
• 10272-07-8 3.5-dimethoxyaniline 
• 379228-26-9 methyl 2-amino-4,6-dimethoxybenzoate 

Downstream Products

• 331662-73-8 4-chloro-5,7-dimethoxy-3-quinolinecarbonitrile 

Relevant articles and documents

Synthesis and Src kinase inhibitory activity of a series of 4-phenylamino-3-quinolinecarbonitriles

Screening of a directed compound library in a yeast-based assay identified 4-[(2,4-dichlorophenyl)amino]-6,7-dimethoxy-3-quinolinecarbonitrile (2a) as a Src inhibitor. An enzymatic assay established that 2a was an ATP-competitive inhibitor of the kinase activity of Src. We present here SAR data for 2a which shows that the aniline group at C-4, the carbonitrile group at C-3, and the alkoxy groups at C-6 and C-7 of the quinoline are crucial for optimal activity. Increasing the size of the C-2 substituent of the aniline at C-4 of 2a from chloro to bromo to iodo resulted in a corresponding increase in Src inhibition. Furthermore, replacement of the 7-methoxy group of 2a with various 3-heteroalkylaminopropoxy groups provided increased inhibition of both Src enzymatic and cellular activity. Compound 25, which contains a 3-morpholinopropoxy group, had an IC50 of 3.8 nM in the Src enzymatic assay and an IC50 of 940 nM for the inhibition of Src-dependent cell proliferation.

Synthesis and structure-activity relationships of 3-cyano-4(phenoxyanilino)quinolines as MEK (MAPKK) inhibitors

A series of 3-cyano-4-(phenoxyanilino)cyanoquinolines has been prepared as MEK (MAP kinase kinase) inhibitors. The best activity is seen with alkoxy groups at both the 6- and 7-positions. The lead compounds show low nanomolar IC50's against MAP kinase kinase, and have potent inhibitory activity in tumor cells. (C) 2000 Elsevier Science Ltd.