100331-89-3

Basic information

• Product Name: 8-BENZYLOXY-5-(2-BROMOACETYL)-2-HYDROXYQUINOLINE
• Synonyms: 8-Benzyloxy-5;8-Benzyloxy-5-(2-broMoacetyl)-2-(1h)-quinoline;2(1H)-Quinolinone, 5-(2-bromoacetyl)-8-(phenylmethoxy)-;Indacaterol Intermediate 2;8-benzyloxy-5-(2-broMoacetyl)-2-(1H)-quinolinone;1-[8-(benzyloxy)-2-hydroxyquinolin-5-yl]-2-broMoethan-1-one;8-(benzyloxy)-5-(2-broMoacetyl)quinolin-2(1H)-one;5-(2-BroMo-1-oxoethyl)-8-benzyloxy-2(1H)-quinolinone
• CAS NO: 100331-89-3
• Molecular Formula: C₁₈H₁₄BrNO₃
• Molecular Weight: 372.21
• EINECS: 1308068-626-2
• Product Categories: Intermediate of Indacaterol;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 100331-89-3.mol

Chemical Properties

• Boiling Point: 602.645 °C at 760 mmHg
• Flash Point: 318.268 °C
• Appearance: Off-white solid
• Density: 1.48 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.638
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• PKA: 10.38±0.70(Predicted)
• Stability: Unstable in DMSO
• CAS DataBase Reference: 8-BENZYLOXY-5-(2-BROMOACETYL)-2-HYDROXYQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-BENZYLOXY-5-(2-BROMOACETYL)-2-HYDROXYQUINOLINE(100331-89-3)
• EPA Substance Registry System: 8-BENZYLOXY-5-(2-BROMOACETYL)-2-HYDROXYQUINOLINE(100331-89-3)

Safety Data

• Hazardous Substances Data: 100331-89-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
8-BENZYLOXY-5-(2-BROMOACETYL)-2-HYDROXYQUINOLINE 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.
Used in Chemical Research:
As a complex organic molecule, 8-BENZYLOXY-5-(2-BROMOACETYL)-2-HYDROXYQUINOLINE can be utilized in chemical research for the development of new compounds with potential applications in various industries. Its unique structure and functional groups make it an interesting candidate for further modification and exploration of its properties and potential uses.
Used in Material Science:
The unique chemical structure of 8-BENZYLOXY-5-(2-BROMOACETYL)-2-HYDROXYQUINOLINE may also find applications in material science, where it could be used to develop new materials with specific properties. For instance, its incorporation into polymers or other materials could lead to the creation of novel materials with enhanced properties, such as improved stability, reactivity, or selectivity.

InChI:InChI=1/C18H14BrNO3/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/h1-9H,10-11H2,(H,20,22)

Upstream product

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

Downstream Products

• 530084-79-8 8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one 
• 1613593-47-7 2-(4-((((R)-2-Hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)amino)methyl)-2-methylphenoxy)ethyl 4-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl)phenoxy)methyl)benzoate 
• 112281-28-4 8-benzyloxy-5-(epoxyethyl)-(1H)-quinolin-2-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.

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.

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.

A Process for Preparing Indacaterol and Salts Thereof

The present invention relates to a process for preparing indacaterol or salts thereof. The process comprises of forming compound of Formula 1 by reacting compound of Formula 2 and compound of Formula 3 in the presence of a solvent to Form compound of Formula 4, which on removal of the protecting groups forms compound of Formula 1.

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

COMPOUNDS HAVING MUSCARINIC RECEPTOR ANTAGONIST AND BETA2 ADRENERGIC RECEPTOR AGONIST ACTIVITY

Compounds of formula I, defined herein, act both as muscarinic receptor antagonists and beta2 adrenergic receptor agonists and are useful for treating broncho-obstructive and inflammatory diseases.

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 pharmaceutical active ingredients.

COMPOUNDS HAVING MUSCARINIC RECEPTOR ANTAGONIST AND BETA2 ADRENERGIC RECEPTOR AGONIST ACTIVITY

Compounds of formula (I) described herein act both as muscarinic receptor antagonists and beta2 adrenergic receptor agonists and are useful for the prevention and/or treatment of broncho-obstructive or inflammatory diseases.

COMPOUNDS HAVING MUSCARINIC RECEPTOR ANTAGONIST AND BETA2 ADRENERGIC RECEPTOR AGONIST ACTIVITY

Compounds of formula (I) defined herein act both as muscarinic receptor antagonists and beta2 adrenergic receptor agonists and are useful for the prevention and/or treatment of broncho-obstructive or inflammatory diseases.

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 pharmaceutical active ingredients.