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

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

Uses

Used in Pharmaceutical Industry:
4-Aminoquinoline-2-one is used as an active pharmaceutical ingredient for the synthesis of antimalarial drugs, given its inherent antimalarial properties. It is also being studied for its potential role in the treatment of Parkinson's disease, as well as its ability to inhibit the enzyme acetylcholinesterase, which is implicated in the progression of Alzheimer's disease.
Used in Dye Industry:
In the dye industry, 4-Aminoquinoline-2-one serves as a key intermediate in the synthesis of various dyes, contributing to the development of a diverse range of colorants for different applications.
Used in Antimicrobial Applications:
4-Aminoquinoline-2-one is used as an antimicrobial agent due to its demonstrated antibacterial and antiviral activities. Its potential in the development of new therapeutic agents against resistant strains of bacteria and viruses is currently under investigation.

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 
• 7664-41-7 ammonia 
• 7732-18-5 water 
• 1885-29-6 anthranilic acid nitrile 
• 703-61-7 2,4-dichloroquinoline 
• 110216-76-7 4-azido-1H-quinolin-2-one 
• 157027-50-4 C₂₇H₂₀ClN₂P 
• 157027-30-0 4-azido-2-chloro-quinoline 
• 833461-40-8 1H-4-amino-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 
• 80356-47-4 4-benzylamino-1H-quinolin-2-one 

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.

MODULATION OF CHEMOSENSORY RECEPTORS AND LIGANDS ASSOCIATED THEREWITH

The present invention provides screening methods for identifying modifiers of chemosensory receptors and their ligands, e.g., by determining whether a test entity is suitable to interact with one or more interacting sites within the Venus flytrap domains of the chemosensory receptors as well as modifiers capable of modulating chemosensory receptors and their ligands.

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

A new application of diphenylphosphorylazide (DPPA) reagent: Convenient transformations of quinolin-4-one, pyridin-4-one and quinazolin-4-one derivatives into the 4-azido and 4-amino counterparts

Herein, we describe a transformation of the oxo-function of a series of quinolin/pyridin/quinazolin-4-ones into 4-azido and thence into 4-amino derivatives in moderate yields by a very short and convenient new procedure using DPPA (diphenylphosphoryl azide) as reagent. A mechanism for this interesting new application of DPPA is suggested based on the identification of some of the intermediates.

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.

Methods for the Synthesis of 4-Azido-2(1H)-quinolones

4-Hydroxy-2-quinolones 1 are generally found to be converted to the 4-azidocompounds 3 via the 4-chloroquinolones 2, the 4-tosyloxyquinolones 6, or the 4-aminoquinolones 4, respectively.Choice of the reaction conditions and yields depend on the substituen