13669-61-9

Basic information

• Product Name: 4-Hydroxy-6-methoxyquinoline-3-carbonitrile
• Synonyms: 4-Hydroxy-6-methoxyquinoline-3-carbonitrile;6-methoxy-4-oxo-1H-quinoline-3-carbonitrile;3-Quinolinecarbonitrile, 4-hydroxy-6-Methoxy-
• CAS NO: 13669-61-9
• Molecular Formula: C11H8N2O2
• Molecular Weight: 200.19342
• Mol File: 13669-61-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 356°Cat760mmHg
• Flash Point: 169.1°C
• Appearance: /
• Density: 1.32g/cm³
• Vapor Pressure: 3.01E-05mmHg at 25°C
• Refractive Index: 1.62
• PKA: 1.21±0.50(Predicted)
• CAS DataBase Reference: 4-Hydroxy-6-methoxyquinoline-3-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxy-6-methoxyquinoline-3-carbonitrile(13669-61-9)
• EPA Substance Registry System: 4-Hydroxy-6-methoxyquinoline-3-carbonitrile(13669-61-9)

Safety Data

• Hazardous Substances Data: 13669-61-9(Hazardous Substances Data)

Usage

General Description

4-Hydroxy-6-methoxyquinoline-3-carbonitrile, also known as Xanthoplanine, is a chemical compound with the molecular formula C11H8N2O3. It is a quinoline derivative with a hydroxyl and methoxy group attached to the aromatic ring, as well as a carbonitrile functional group. 4-Hydroxy-6-methoxyquinoline-3-carbonitrile has been found to exhibit potential pharmacological properties, including antimicrobial and anti-inflammatory activities. It has also been studied for its potential use in the treatment of various diseases and disorders. Additionally, 4-Hydroxy-6-methoxyquinoline-3-carbonitrile has been reported to have antioxidant properties, making it of interest for further research and development in the field of pharmaceuticals.

InChI:InChI=1/C11H8N2O2/c1-15-8-2-3-10-9(4-8)11(14)7(5-12)6-13-10/h2-4,6H,1H3,(H,13,14)

Upstream product

• 7507-86-0 2-bromo-5-methoxy-benzaldehyde 
• 50-00-0 formaldehyd 
• 2475-80-1 methyl 2-amino-5-methoxybenzoate 
• 394-31-0 2-amino-5-hydroxybenzoic acid 
• 75-05-8 acetonitrile 
• 872714-53-9 (E)-methyl 2-(((dimethylamino)methylene)amino)-5-methoxybenzoate 
• 20428-58-4 α-lithioacetonitrile 

Downstream Products

• 13669-62-0 4-chloro-6-methoxy-quinoline-3-carbonitrile 
• 872714-52-8 4-bromo-6-(methyloxy)-3-quinolinecarbonitrile 

Relevant articles and documents

Copper-Catalyzed Synthesis of Substituted 4-Quinolones using Water as a Benign Reaction Media: Application for the Construction of Oxolinic Acid and BQCA

A copper-catalyzed three-component synthetic method has been developed for the synthesis of substituted 4-quinolone derivatives from substituted 3-(2-halophenyl)-3-oxopropane, aldehydes and aq. NH3 using water as an environmentally benign reaction media. Moreover, the synthetic utility of the obtained products has been successfully applied for the synthesis of available oxolinic acid and BQCA drugs. The key features of this approach include commercially available starting materials, broad scope, and moderate to good reaction yields. Reaction with formaldehyde, and other functionalities such as ?CN, ?NO2, ?SO2Ar, and ?COAr were also successful. In addition, reaction with heterocyclic compounds such as 3-(3-bromothiophen-2-yl)-3-oxopropanenitrile proceeded smoothly to afford tetrahydrothieno[3,2-b]pyridine-6-carbonitrile analogues. The practicality of the designed protocol was confirmed by gram scale synthesis of two derivatives. (Figure presented.).

ANTIVIRAL AGENTS

Compounds are provided having utility for the treatment of viral infections, particularly HCV.

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.