530084-79-8

Basic information

• Product Name: 8-Benzyloxy-5-((R)-2-broMo-1-hydroxyethyl)-1H-quinolinone
• Synonyms: 8-benzyloxy-5((R)-2-broMo-1-hydroxyethyl)-2-(1H-)-quinolinone;(R)-8-Benzyloxy-5-(2-broMo-1-hydroxyethyl)carbostyril;5-(2-BroMo-(R)-1-hydroxyethyl)-8-benzyloxy-2(1H)-quinolinone;5-[(1R)-2-BroMo-1-hydroxyethyl]-8-(phenylMethoxy)-2(1H)-quinolinone;8-(Benzylox;(R)-8-(Benzyloxy)-5-(2-broMo-1-hydroxyethyl)quinolin-2(1H)-one;8-Benzyloxy-5((R)-2-broMo-1-hydroxyethyl)-2-(1H)-quinoline;8-Benzyloxy-5-((R)-2-broMo-1-hydroxyethyl)-1H-quinolin-2-one
• CAS NO: 530084-79-8
• Molecular Formula: C₁₈H₁₆BrNO₃
• Molecular Weight: 374.22854
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics
• Mol File: 530084-79-8.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 595.764 °C at 760 mmHg
• Flash Point: 314.107 °C
• Appearance: /
• Density: 1.491 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.649
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO (Slightly), Ethyl Acetate (Slightly)
• PKA: 10.78±0.70(Predicted)
• CAS DataBase Reference: 8-Benzyloxy-5-((R)-2-broMo-1-hydroxyethyl)-1H-quinolinone(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Benzyloxy-5-((R)-2-broMo-1-hydroxyethyl)-1H-quinolinone(530084-79-8)
• EPA Substance Registry System: 8-Benzyloxy-5-((R)-2-broMo-1-hydroxyethyl)-1H-quinolinone(530084-79-8)

Safety Data

• Hazardous Substances Data: 530084-79-8(Hazardous Substances Data)

Usage

Description

8-Benzyloxy-5-((R)-2-bromo-1-hydroxyethyl)-1H-quinolinone is a light brown solid with a complex chemical structure. It is a derivative of quinolinone, a heterocyclic compound with potential applications in various fields due to its unique properties.

Uses

Used in Pharmaceutical Industry:
8-Benzyloxy-5-((R)-2-bromo-1-hydroxyethyl)-1H-quinolinone is used as a key intermediate in the synthesis of phenylethanolamine derivatives, which are known as β2 adrenoreceptor agonists. These agonists play a crucial role in the treatment of various medical conditions, such as asthma and chronic obstructive pulmonary disease (COPD), by relaxing the smooth muscles in the airways and improving lung function.
As a β2 adrenoreceptor agonist, 8-Benzyloxy-5-((R)-2-bromo-1-hydroxyethyl)-1H-quinolinone contributes to the development of new drugs that can help manage respiratory disorders more effectively. Its chemical properties make it a valuable compound in the pharmaceutical industry for creating innovative and potent medications.

InChI:InChI=1/C18H16BrNO3/c19-10-15(21)13-6-8-16(18-14(13)7-9-17(22)20-18)23-11-12-4-2-1-3-5-12/h1-9,15,21H,10-11H2,(H,20,22)/t15-/m0/s1

Upstream product

• 100331-89-3 8-benzyloxy-5-bromoacetylcarbostyril 
• 112022-83-0 (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole 
• 1127-45-3 8-Hydroxyquinoline-N-oxide 
• 148-24-3 8-quinolinol 
• 15450-72-3 2-oxo-1,2-dihydroquinolin-8-yl acetate 
• 62978-73-8 5-acetyl-8-hydroxy-2(1H)-quinolinone 
• 93609-84-8 5-acetyl-8-benzyloxy-1H-quinolin-2-one 
• 100331-89-3 8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one 
• 15450-76-7 8-Hydroxy-1H-quinolin-2-one 
• 100-39-0 benzyl bromide 
• 57434-96-5 5-acetyl-8-hydroxyquinoline hydrochloride 
• 100331-93-9 5-Acetyl-8-benzyloxyquinoline-N-oxide 
• 26872-48-0 1-(8-benzyloxyquinolin-5-yl)ethanone 
• 2598-31-4 5-acetyl-8-hydroxyquinoline 

Downstream Products

• 530084-74-3 (R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-one 
• 1254097-58-9 4-({[5-(2-{[4-({[(2R)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino}methyl)phenyl]carbamoyl}ethyl)-2-phenylphenyl]carbamoyl}oxy)-1,1-dimethylpiperidin-1-ium trifluoroacetate 
• 1254098-73-1 4-[({5-[(8-{[(2R)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino}octyl)oxy]-2-phenylphenyl}carbamoyl)oxy]-1,1-dimethylpiperidin-1-ium trifluoroacetate 
• 1254098-93-5 4-({[5-(2-{[4-(2-{[(2R)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino}-2-methylpropyl)phenyl]carbamoyl}ethyl)-2-phenylphenyl]carbamoyl}oxy)-1,1-dimethylpiperidin-1-ium trifluoroacetate 
• 1254099-09-6 4-({[5-(9-{[(2R)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino}nonyl)-2-phenylphenyl]carbamoyl}oxy)-1,1-dimethylpiperidin-1-ium trifluoroacetate 
• 1254103-10-0 4-({[5-(9-[{(2R)-[8-(benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl]-2-hydroxyethyl}amino]nonyl)-2-phenylphenyl]carbamoyl}oxy)-1,1-dimethylpiperidin-1-ium trifluoroacetate 
• 1254099-13-2 4-{[(5-{3-[(5-{[(2R)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino}pentyl)oxy]propyl}-2-phenylphenyl)carbamoyl]oxy}-1,1-dimethylpiperidin-1-ium trifluoroacetate 
• 100429-06-9 8-benzyloxy-5-{(1R)-1-hydroxy-2-[N-((1R)-2-(p-methoxyphenyl)-1-methylethyl)amino]ethyl}carbostyril 
• 1052689-06-1 8-benzyloxy-5-{(1R)-1-hydroxy-2-[N-((lR)-2-(p-methoxy phenyl)-1-methylethyl) amino] ethyl} carbostyril hydrochloride 
• 100429-08-1 8-hydroxy-5-((1R)-1-hydroxy-2-(N-((1R)-2-(4-methoxyphenyl)-1-methylethyl)amino)ethyl)carbostyril hydrochloride 
• 662111-65-1 8-benzyloxy-5-[(R)-2-benzylamino-1-hydroxyethyl]-(1H)-quinolin-2-one 
• 948895-02-1 8-(benzyloxy)-5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({[4-hydroxy-1-(4-phenoxybutyl)piperidin-4-yl]methyl}amino)ethyl]quinolin-2(1H)-one 
• 948895-60-1 5-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-{[(1-{2-[2-(2,6-dichlorophenyl)ethoxy]ethyl}-4-hydroxypiperidin-4-yl)methyl]amino}ethyl)-8-hydroxyquinolin-2(1H)-one 
• 948894-41-5 8-(benzyloxy)-5-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-[({4-methoxy-1-[2-(2-phenylethoxy)ethyl]piperidin-4-yl}methyl)amino]ethyl}quinolin-2(1H)-one 

Relevant articles and documents

Discovery of a novel class of inhaled dual pharmacology muscarinic antagonist and β2 agonist (MABA) for the treatment of chronic obstructive pulmonary disease (COPD)

The targeting of both the muscarinic and β-adrenergic pathways is a well validated therapeutic approach for the treatment of chronic obstructive pulmonary disease (COPD). In this communication we report our effort to incorporate two pharmacologies into a single chemical entity, whose characteristic must be suitable for a once daily inhaled administration. Contextually, we aimed at a locally acting therapy with limited systemic absorption to minimize side effects. Our lung-tailored design of bifunctional compounds that combine the muscarinic and β-adrenergic pharmacologies by the elaboration of the muscarinic inhibitor 7, successfully led to the potent, pharmacologically balanced muscarinic antagonist and β2 agonist (MABA) 13.

CLASS OF BIFUNCTIONAL COMPOUNDS WITH QUATERNARY AMMONIUM SALT STRUCTURE

The invention provides a class of compounds represented by formula (I), having bifunctional active quaternary ammonium salt structure of a β2-adrenoreceptor agonist and an M receptor antagonist, a pharmaceutically acceptable salt, solvate, and optical isomer thereof. A pharmaceutical composition comprising such a compound with quaternary ammonium salt structure, a method for preparing such a compound with quaternary ammonium salt structure and an intermediate thereof, and uses thereof in treating pulmonary disorders are also provided. The compounds of the invention have high selectivity to the M receptor subtype, and have less adverse reaction and lower toxic and side effects in the treatment of pulmonary diseases such as COPD and asthma.

COMPOUNDS HAVING MUSCARINIC RECEPTOR ANTAGONIST AND BETA2 ADRENERGIC RECEPTOR AGONIST ACTIVITY

The present invention relates to compounds acting both as muscarinic receptor antagonists and beta2 adrenergic receptor agonists, to processes for their preparation, to compositions comprising them, to therapeutic uses and combinations with other pharmace