110216-87-0

Basic information

• Product Name: 4-AMINOQUINOLINE-2-ONE
• Synonyms: 4-AMINOQUINOLINE-2-ONE;AURORA KA-3886;Zinc02550723;4-Amino-2(1H)-quinolinone;4-Aminoquinolin-2(1H)-one;2(1H)-Quinolinone, 4-amino-
• CAS NO: 110216-87-0
• Molecular Formula: C₉H₈N₂O
• Molecular Weight: 160.17
• Mol File: 110216-87-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 315℃
• Boiling Point: 393℃
• Flash Point: 191℃
• Appearance: /
• Density: 1.254
• Vapor Pressure: 2.28E-06mmHg at 25°C
• Refractive Index: 1.623
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 11.27±0.70(Predicted)
• CAS DataBase Reference: 4-AMINOQUINOLINE-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINOQUINOLINE-2-ONE(110216-87-0)
• EPA Substance Registry System: 4-AMINOQUINOLINE-2-ONE(110216-87-0)

Safety Data

• Hazardous Substances Data: 110216-87-0(Hazardous Substances Data)

Usage

General Description

4-Aminoquinoline-2-one is a chemical compound with the molecular formula C9H8N2O. It is a yellow crystalline solid with a faint odor. 4-AMINOQUINOLINE-2-ONE is used in the synthesis of dyes and pharmaceuticals, and it also exhibits antimalarial properties. 4-Aminoquinoline-2-one has been studied for its potential role in the treatment of Parkinson's disease and as an inhibitor of the enzyme acetylcholinesterase, which is involved in the progression of Alzheimer's disease. Additionally, it has been investigated for its antibacterial and antiviral activities, making it a compound of interest in the development of new therapeutic agents.

InChI:InChI=1/C9H8N2O/c10-7-5-9(12)11-8-4-2-1-3-6(7)8/h1-5H,(H3,10,11,12)

Upstream product

• 70254-44-3 2,4-dihydroxyquinoline 
• 50786-32-8 4-Amino-2-ethoxy-chinolin 
• 25116-00-1 2-acetamidobenzonitrile 
• 70254-43-2 4-Hydroxy-2-quinolone 
• 703-61-7 2,4-dichloroquinoline 
• 833461-40-8 1H-4-amino-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 
• 110216-76-7 4-azido-1H-quinolin-2-one 
• 157027-50-4 C₂₇H₂₀ClN₂P 
• 80356-47-4 4-benzylamino-1H-quinolin-2-one 
• 1885-29-6 anthranilic acid nitrile 
• 7664-41-7 ammonia 
• 7732-18-5 water 
• 157027-30-0 4-azido-2-chloro-quinoline 

Relevant articles and documents

Synthesis of aryl-heteroaryl ureas (AHUs) based on 4-aminoquinoline and their evaluation against the insulin-like growth factor receptor (IGF-1R)

The insulin-like growth factor receptor (IGF-1R) is a receptor tyrosine kinase (RTK) involved in all stages of the development and propagation of breast and other cancers. The inhibition of IGF-1R by small molecules remains a promising strategy to treat cancer. Herein, we explore SAR around previously characterized lead compound (1), which is an aryl-heteroaryl urea (AHU) consisting of 4-aminoquinaldine and a substituted aromatic ring system. A library of novel AHU compounds was prepared based on derivatives of the 4-aminoquinoline heterocycle (including various 2-substituted derivatives, and naphthyridines). The compounds were screened for in vitro inhibitory activity against IGF-1R, and several compounds with improved activity (3-5 μM) were identified. Furthermore, a computational docking study was performed, which identifies a fairly consistent lowest energy mode of binding for the more-active set of inhibitors in this series, while the less-active inhibitors do not adopt a consistent mode of binding.

4-Hydroxy-2-quinolones. 93. Synthesis and biological properties of 2-hydroxy-4-imino-1,4-dihydroquinoline-3-carboxylic acid N-R-amides

Various methods of synthesizing amides of 2-hydroxy-4-imino-1,4- dihydroquinoline-3-carboxylic acids have been studied. Results of investigations on the antitubercular and antiinflammatory activity of the obtained compounds are discussed. 2006 Springer Sc

Regioselective Azidation of 2,4-Dichloroquinolines

Reactions of 2,4-dichloroquinolines (2a-f) with sodium azide in DMF lead either regioselectively to 4-azido-2-chloroquinolines (3a-f) or with excess of sodium azide and catalysts to 5-azido-tetrazoloquinolines (4a-f). 2,4-Dichloroquinolines (2g-i) having electron donating substituents in 3-position react with sodium azide in DMF to a mixture of 4-azido-2-chloroquinolines (3g-i) and 5-chlorotetrazoloquinolines (5g-i).When the reaction of the 2,4-dichloroquinolines (2a-i) with sodium azide is carried out in ethanol with addition of methanesulfonic acid, regioselectively 5-chloro-tetrazoloquinolines (5a-i) are obtained.Structural assignments of 3 and 5 have been carried out by 13C-NMR spectra, IR spectra and degradation reactions of the azido- and tetrazolo group to aminoquinolines (7 and 10) via iminophosphoranes (8 and 9).It could be shown that in 2-azido/tetrazolo-quinolines (4 and 5) the tetrazole ring structure is the dominant species.