61317-32-6

Usage

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

Downstream Products

• 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 
• 1268334-12-8 5-(piperazin-1-yl)-1H-quinolin-2-one 
• 1002125-08-7 (2E,4Z)-5-(4-ethoxyphenyl)-N-(2-oxo-1,2-dihydro-5-quinolyl)-5-(4-trifluoromethylphenyl)-2,4-pentadienamide 
• 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 
• 1263417-93-1 5-{[4-(3-ethyl-2-methoxyphenyl)-2-hydroxy-3-methyl-2-(trifluoromethyl)pentylidene]amino}-1H-quinolin-2-one 
• 950519-81-0 5-{[4-(4-isopropyl-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)hexylidene]amino}-1H-quinolin-2-one 

Relevant academic research and scientific papers

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.

N-(4-acetamidophenyl)-5-acetylfuran-2-carboxamide as a novel orally available diuretic that targets urea transporters with improved PD and PK properties

Urea transporters (UTs) have been identified as new targets for diuretics. Functional deletion of UTs led to urea-selective urinary concentrating defects with relative salt sparing. In our previous study, a UT inhibitor with a diarylamide scaffold, which is denoted as 11a, was demonstrated as the first orally available UT inhibitor. However, the oral bioavailability of 11a was only 4.38%, which obstructed its clinical application. In this work, by replacing the nitro group of 11a with an acetyl group, 25a was obtained. Compared with 11a, 25a showed a 10 times stronger inhibitory effect on UT-B (0.14 μM vs. 1.41 μM in rats, and 0.48 μM vs. 5.82 μM in mice) and a much higher inhibition rate on UT-A1. Moreover, the metabolic stability both in vitro and in vivo and the drug-like properties (permeability and solubility) of 25a were obviously improved compared with those of 11a. Moreover, the bioavailability of 25a was 15.18%, which was 3 times higher than that of 11a, thereby resulting in significant enhancement of the diuretic activities in rats and mice. 25a showed excellent potential for development as a promising clinical diuretic candidate for targeting UTs to treat diseases that require long-term usage of diuretics, such as hyponatremia.

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.

CHROMONE DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATIONS

The present invention relates to chromone derivatives, their preparation, their pharmaceutical compositions and their application as D3 dopaminergic ligands as a medicament for disorders of the central nervous system.

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.

4'-AMINO CYCLIC COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY

The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): formula (I) wherein Cy is selected from formula (Il) and wherein R1, R2, R3, Q, G, Ar, m, n 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.

3' SUBSTITUTED 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 Q, R1, R4, m and Ar are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.

TRICYCLIC AMINOALCOHOLS, METHODS FOR PRODUCING THE SAME AND THEIR USE AS ANTI-INFLAMMATORY AGENTS

The invention relates to the tricyclic aminoalcohols of general formula (I), to methods for producing the same and to their use as anti-inflammatory agents.

ALKYLIDENE TETRAHYDRONAPHTHALENE DERIVATIVES, METHOD FOR THEIR PRODUCTION AND THEIR USE AS ANTI-INFLAMMATORY AGENTS

The invention relates to alkylidene tetrahydronaphthalene derivatives of general formula (I), to methods for their production and to their use as anti-inflammatory agents.

TETRAHYDRONAPHTHALENE DERIVATIVES, METHOD FOR THEIR PRODUCTION AND THEIR USE AS ANTI-INFLAMMATORY AGENTS

The invention relates to tetrahydronaphthalene derivatives of general formula (I), to a method for their production and to their use as anti-inflammatory agents.