62978-73-8

Basic information

• Product Name: 5-ACETYL-8-HYDROXY-1H-QUINOLIN-2-ONE
• Synonyms: 5-ACETYL-8-HYDROXY-1H-QUINOLIN-2-ONE;5-ACETYL-QUINOLINE-2,8-DIOL;5-Acetyl-8-hydroxy-2(1H)-quinolinone;5-Acetyl-1,2-dihydro-8-hydroxy-2-oxoquinoline, 1-(1,2-Dihydro-8-hydroxy-2-oxoquinolin-5-yl)ethan-1-one;5-Acetyl-8-hydroxyquinolin-2(1H)-one;5-acetyl-8-hydroxy-1,2-dihydroquinolin-2-one;2(1H)-Quinolinone, 5-acetyl-8-hydroxy-;5-Acetyl-8-hydroxycarbostyril
• CAS NO: 62978-73-8
• Molecular Formula: C₁₁H₉NO₃
• Molecular Weight: 203.19
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 62978-73-8.mol
• Article Data: 17

Chemical Properties

• Melting Point: >260℃
• Boiling Point: 509.485 °C at 760 mmHg
• Flash Point: 261.927 °C
• Appearance: /
• Density: 1.336
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.62
• CAS DataBase Reference: 5-ACETYL-8-HYDROXY-1H-QUINOLIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-ACETYL-8-HYDROXY-1H-QUINOLIN-2-ONE(62978-73-8)
• EPA Substance Registry System: 5-ACETYL-8-HYDROXY-1H-QUINOLIN-2-ONE(62978-73-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Hazardous Substances Data: 62978-73-8(Hazardous Substances Data)

Usage

Uses

5-Acetylquinoline-2,8-diol can be used in the preparation of 5-Acetylcarbostyril oxime derivatives as β2 adrenoreceptor agonists.

InChI:InChI=1/C11H9NO3/c1-6(13)7-2-4-9(14)11-8(7)3-5-10(15)12-11/h2-5,14H,1H3,(H,12,15)

Upstream product

• 15450-72-3 2-oxo-1,2-dihydroquinolin-8-yl acetate 
• 15450-76-7 8-Hydroxy-1H-quinolin-2-one 
• 75-36-5 acetyl chloride 
• 148-24-3 8-quinolinol 
• 1127-45-3 8-Hydroxyquinoline-N-oxide 
• 108-24-7 acetic anhydride 
• 22614-69-3 8-methoxy-1H-quinolin-2-one 
• 62978-76-1 acetyl-5 methoxy-8 carbostyrile 

Downstream Products

• 1254102-83-4 5-(2-bromoacetyl)-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one 
• 1254102-84-5 5-[(1R)-2-bromo-1-hydroxyethyl]-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one 
• 1254098-87-7 4-[({5-[2-({[4-({[(2R)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino}methyl)phenyl]methyl}carbamoyl)ethyl]-2-phenylphenyl}carbamoyl)oxy]-1,1-dimethylpiperidin-1-ium trifluoroacetate 
• 100331-89-3 8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one 
• 112281-28-4 8-benzyloxy-5-(epoxyethyl)-(1H)-quinolin-2-one 
• 956235-29-3 tert-butyl benzyl[2-({6-[(2-hydroxy-2-{8-[(4-methoxybenzyl)oxy]-2-oxo-1,2-dihydroquinolin-5-yl}ethyl)amino]hexyl}oxy)ethyl]carbamate 
• 956235-10-2 {8-[(4-methoxybenzyl)oxy]-2-oxo-1,2-dihydroquinolin-5-yl}(oxo)acetaldehyde 
• 753498-25-8 indacaterol maleate 
• 312753-06-3 indacaterol 
• 435273-75-9 (R)-8-(benzyloxy)-5-[2-[(5,6-diethyl-2,3-dihydro-1H-indole-2-yl)amino]-1-hydroxyethyl]quinolin-2(1H)-one 
• 774222-23-0 5-(R)-(2-amino-1-hydroxy-ethyl)-8-phenylmethoxy-(1H)-quinolin-2-one 

Relevant articles and documents

Novel Quinolone Derivatives: Synthesis and Antioxidant Activity

Abstract: Novel quinolone derivatives have been designed and readily synthesized according to a simple protocol including O-alkylation and Claisen rearrangement processes. Structures of the synthesized compounds have been confirmed by IR, 1H and 13C NMR, and mass spectra. The new products have been tested for their antioxidant activity, and two of those demonstrate high antioxidant activity.

Discovery of β-arrestin-biased β2-adrenoceptor agonists from 2-amino-2-phenylethanol derivatives

β-Arrestins are a small family of proteins important for signal transduction at G protein-coupled receptors (GPCRs). β-Arrestins are involved in the desensitization of GPCRs. Recently, biased ligands possessing different efficacies in activating the G protein- versus the β-arrestin-dependent signals downstream of a single GPCR have emerged, which can be used to selectively modulate GPCR signal transduction in such a way that desirable signals are enhanced to produce therapeutic effects while undesirable signals of the same GPCR are suppressed to avoid side effects. In the present study, we evaluated agonist bias for compounds developed along a drug discovery project of β2-adrenoceptor agonists. About 150 compounds, including derivatives of fenoterol, 2-amino-1-phenylethanol and 2-amino-2-phenylethanol, were obtained or synthesized, and initially screened for their β-adrenoceptor-mediated activities in the guinea pig tracheal smooth muscle relaxation assay or the cardiomyocyte contractility assay. Nineteen bioactive compounds were further assessed using both the HTRF cAMP assay and the PathHunter β-arrestin assay. Their concentration-response data in stimulating cAMP synthesis and β-arrestin recruitment were applied to the Black–Leff operational model for ligand bias quantitation. As a result, three compounds (L-2, L-4, and L-12) with the core structure of 5-(1-amino-2-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one were identified as a new series of β-arrestin-biased β2-adrenoceptor agonists, whereas salmeterol was found to be Gs-biased. These findings would facilitate the development of novel drugs for the treatment of both heart failure and asthma.

Compounds having beta adrenergic receptor agonist and muscarinic receptor antagonist activity

This invention provides compounds of formula I: wherein R1, R2, R4, R5, R6, R7, R8a, R8b, W, a, b, c and m are as defined in the specification, or a pharmaceutically acceptable salt or solvate or stereoisomer thereof. The compounds of this invention possess both β2 adrenergic receptor agonist and muscarinic receptor antagonist activity. Accordingly, such compounds are expected to be useful as therapeutic agents for treating pulmonary disorders, such as chronic obstructive pulmonary disease and asthma.