61317-32-6

Basic information

• Product Name: 5-Amino-2(1H)-quinolinone
• Synonyms: 5-Amino-2(1H)-quinolinone;5-aMinoquinolin-2(1H)-one;5-amino-1H-quinolin-2-one
• CAS NO: 61317-32-6
• Molecular Formula: C₉H₈N₂O
• Molecular Weight: 160.17
• Product Categories: Aromatics, Heterocycles, Intermediates
• Mol File: 61317-32-6.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 416.7±45.0 °C(Predicted)
• Appearance: /
• Density: 1.287±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 11.42±0.70(Predicted)
• CAS DataBase Reference: 5-Amino-2(1H)-quinolinone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Amino-2(1H)-quinolinone(61317-32-6)
• EPA Substance Registry System: 5-Amino-2(1H)-quinolinone(61317-32-6)

Safety Data

• Hazardous Substances Data: 61317-32-6(Hazardous Substances Data)

Usage

Description

5-Amino-2(1H)-quinolinone is an organic compound that serves as an intermediate in the synthesis of various pharmaceuticals and chemical compounds. It is characterized by the presence of an amino group attached to the quinoline ring, which contributes to its unique chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
5-Amino-2(1H)-quinolinone is used as an intermediate in the synthesis of transient receptor potential vanilloid 1 (TRPV1) antagonists. These antagonists are orally available and have potential applications in treating pain and inflammation, as TRPV1 receptors play a crucial role in the perception of pain and thermal sensations.
In the synthesis process, 5-Amino-2(1H)-quinolinone can be further modified and combined with other chemical entities to create TRPV1 antagonists with improved pharmacological properties, such as increased potency, selectivity, and bioavailability. This makes it a valuable component in the development of novel therapeutic agents for pain management and other related conditions.

Upstream product

• 6938-27-8 5-nitroquinolin-2-ol 
• 607-34-1 5-nitroquinoline 
• 6938-27-8 5-nitro-2<1H>quinolinone 
• 612-62-4 2-Chloroquinoline 
• 13067-94-2 2-chloro-5-nitroquinoline 
• 7613-19-6 5-nitro-quinoline-1-oxide 

Downstream Products

• 950519-81-0 5-{[4-(4-isopropyl-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)hexylidene]amino}-1H-quinolin-2-one 
• 1263417-93-1 5-{[4-(3-ethyl-2-methoxyphenyl)-2-hydroxy-3-methyl-2-(trifluoromethyl)pentylidene]amino}-1H-quinolin-2-one 
• 879339-22-7 5-[3-[1-(3-fluoro-2-methoxyphenyl)-cyclopropyl]-2-hydroxy-2-trifluoromethyl-propylimino]-quinolin-2(1H)-one 
• 879339-31-8 5-[(2-hydroxy-4-phenyl-2-trifluoromethyl-hept-4-en-1-yl)imino]-quinolin-2(1H)-one 
• 1152781-76-4 5-{[1-(2-fluoro-4-methoxyphenyl)-methylidene]amino}-1H-quinolin-2-one 
• 1152781-75-3 5-[(3,3,3-trifluoro-2-hydroxy-2-methoxymethyl-1-phenylpropylidene)amino]-1H-quinolin-2-one 
• 1161857-26-6 C₂₃H₂₃F₃N₂O₃ 
• 1161857-07-3 5-{[4-(3-chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyliden]amino}-1H-quinoline-2-one 

Relevant articles and documents

Discovery of Benzopyridone-Based Transient Receptor Potential Vanilloid 1 Agonists and Antagonists and the Structural Elucidation of Their Activity Shift

Among a series of benzopyridone-based scaffolds investigated as human transient receptor potential vanilloid 1 (TRPV1) ligands, two isomeric benzopyridone scaffolds demonstrated a consistent and distinctive functional profile in which 2-oxo-1,2-dihydroquinolin-5-yl analogues (e.g., 2) displayed high affinity and potent antagonism, whereas 1-oxo-1,2-dihydroisoquinolin-5-yl analogues (e.g., 3) showed full agonism with high potency. Our computational models provide insight into the agonist-antagonist boundary of the analogues suggesting that the Arg557 residue in the S4-S5 linker might be important for sensing the agonist binding and transmitting signals. These results provide structural insights into the TRPV1 and the protein-ligand interactions at a molecular level.

Synthesis and structure-activity relationships of quinolinone and quinoline-based P2X7 receptor antagonists and their anti-sphere formation activities in glioblastoma cells

Screening a compound library of quinolinone derivatives identified compound 11a as a new P2X7 receptor antagonist. To optimize its activity, we assessed structure-activity relationships (SAR) at three different positions, R1, R2 and R3, of the quinolinone scaffold. SAR analysis suggested that a carboxylic acid ethyl ester group at the R1 position, an adamantyl carboxamide group at R2 and a 4-methoxy substitution at the R3 position are the best substituents for the antagonism of P2X7R activity. However, because most of the quinolinone derivatives showed low inhibitory effects in an IL-1β ELISA assay, the core structure was further modified to a quinoline skeleton with chloride or substituted phenyl groups. The optimized antagonists with the quinoline scaffold included 2-chloro-5-adamantyl-quinoline derivative (16c) and 2-(4-hydroxymethylphenyl)-5-adamantyl-quinoline derivative (17k), with IC50 values of 4 and 3 nM, respectively. In contrast to the quinolinone derivatives, the antagonistic effects of the quinoline compounds (16c and 17k) were paralleled by their ability to inhibit the release of the pro-inflammatory cytokine, IL-1β from LPS/IFN-γ/BzATP-stimulated THP-1 cells (IC50 of 7 and 12 nM, respectively). In addition, potent P2X7R antagonists significantly inhibited the sphere size of TS15-88 glioblastoma cells.

CONDENSED HETEROCYCLIC COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY

The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I) wherein R1, A, B, D, E, G, Q, Ar, n, m, and p are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.