203395-59-9

Basic information

• Product Name: 7-(4-BROMOBUTOXY)-QUINOLINE-2(1H)-ONE
• Synonyms: 7-(4-BroMobutoxy)-2(1H)-quinolinone;Aripiprazole BroMo IMpurity;2(1H)-Quinolinone,7-(4- broMobutoxy)-;7-(4-bromobutoxy)quinolin-2(1H)-one;7-(4-BROMOBUTOXY)-QUINOLINE-2(1H)-ONE (Related Reference);7-(4-Bromobutoxy)-1H-quinolin-2-one;7-(4-BROMOBUTOXY)-QUINOLINE-2(1H)-ONE
• CAS NO: 203395-59-9
• Molecular Formula: C₁₃H₁₄BrNO₂
• Molecular Weight: 296.15976
• Product Categories: Aromatics Compounds;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 203395-59-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: 126-128 °C
• Boiling Point: 475.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.418±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Dichloromethane
• PKA: 11.21±0.70(Predicted)
• CAS DataBase Reference: 7-(4-BROMOBUTOXY)-QUINOLINE-2(1H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-(4-BROMOBUTOXY)-QUINOLINE-2(1H)-ONE(203395-59-9)
• EPA Substance Registry System: 7-(4-BROMOBUTOXY)-QUINOLINE-2(1H)-ONE(203395-59-9)

Safety Data

• Hazardous Substances Data: 203395-59-9(Hazardous Substances Data)

Usage

Uses

Aripiprazole Bromo Impurity

Upstream product

• 129722-34-5 7-(4-bromobutoxy)-3,4-dihydro-2(1H)-quinolinone 
• 37783-33-8 7-(4-bromobutoxy)-2H-chromen-2-one 
• 110-52-1 1,4-dibromo-butane 
• 70500-72-0 7-hydroxy-1H-quinolin-2-one 
• 15116-41-3 N-(3-methoxyphenyl)cinnamamide 
• 536-90-3 m-Anisidine 

Downstream Products

• 1354030-31-1 7-(4-(4-(2-methoxyphenyl)-1,4-diazepan-1-yl)butoxy)quinolin-2(1H)-one 
• 913611-97-9 Brexpiprazole 
• 129722-25-4 OPC 14857 
• 1354030-42-4 7-(4-(4-(2-isopropoxyphenyl)-1,4-diazepan-1-yl)butoxy)quinolin-2(1H)-one 
• 1354030-37-7 7-(4-(4-(2-ethoxyphenyl)-1,4-diazepan-1-yl)butoxy)quinolin-2(1H)-one 
• 1354030-20-8 7-(4-(4-(2,3-dichlorophenyl)-1,4-diazepan-1-yl)butoxy)quinolin-2(1H)-one 
• 1314032-23-9 7-(4-(4-(2-(2-fluoroethoxy)phenyl)piperazin-1-yl)butoxy)quinolin-2(1H)-one 

Relevant articles and documents

Identification, Synthesis, and Control of Process-Related Impurities in the Antipsychotic Drug Substance Brexpiprazole

This article describes the identification, synthesis, and control of several unknown related substances present in the form of critical impurities that were observed during the process development for the antipsychotic drug substance brexpiprazole (BRX). On the basis of liquid chromatography-mass spectrometry (LC-MS) evidence of impurities and analysis of the employed synthetic route of BRX, the structures of the unknown impurities were proposed. Many critical impurities were synthesized, and their chemical structures were established using different spectroscopy techniques. To the best of our knowledge, this is the first report where several new impurities were recognized, addressed, and controlled effectively during the development of a robust and efficient process for the BRX drug substance.

Design, synthesis and evaluation of quinolinone derivatives containing dithiocarbamate moiety as multifunctional AChE inhibitors for the treatment of Alzheimer’s disease

A series of novel quinolinone derivatives bearing dithiocarbamate moiety were designed and synthesised as multifunctional AChE inhibitors for the treatment of AD. Most of these compounds exhibited strong and clearly selective inhibition to eeAChE. Among them, compound 4c was identified as the most potent inhibitor to both eeAChE and hAChE (IC50 = 0.22 μM for eeAChE; IC50 = 0.16 μM for hAChE), and it was also the best inhibitor to AChE-induced Aβ aggregation (29.02% at 100 μM) and an efficient inhibitor to self-induced Aβ aggregation (30.67% at 25 μM). Kinetic and molecular modelling studies indicated that compound 4c was a mixed-type inhibitor, which could interact simultaneously with the catalytic anionic site (CAS) and the peripheral anionic site (PAS) of AChE. In addition, 4c had good ability to cross the BBB, showed no toxicity on SH-SY5Y neuroblastoma cells and was well tolerated in mice at doses up to 2500 mg/kg (po).

Acetylcholinesterase inhibition of diversely functionalized quinolinones for alzheimer’s disease therapy

In this communication, we report the synthesis and cholinesterase (ChE)/monoamine oxidase (MAO) inhibition of 19 quinolinones (QN1-19) and 13 dihydroquinolinones (DQN1-13) designed as potential multitarget small molecules (MSM) for Alzheimer’s disease therapy. Contrary to our expectations, none of them showed significant human recombinant MAO inhibition, but compounds QN8, QN9, and DQN7 displayed promising human recombinant acetylcholinesterase (hrAChE) and butyrylcholinesterase (hrBuChE) inhibition. In particular, molecule QN8 was found to be a potent and quite selective non-competitive inhibitor of hrAChE (IC50 = 0.29 μM), with Ki value in nanomolar range (79 nM). Pertinent docking analysis confirmed this result, suggesting that this ligand is an interesting hit for further investigation.

Oxidative Aromatization of 3,4-Dihydroquinolin-2(1 H)-ones to Quinolin-2(1 H)-ones Using Transition-Metal-Activated Persulfate Salts

Inorganic persulfate salts were identified as efficient reagents for the oxidative aromatization of 3,4-dihydroquinolin-2(1H)-ones through the activation of readily available transition metals, such as iron and copper. The feasible protocol conforming to the requirement of green chemistry was utilized in the preparation of the key intermediate (7-(4-chlorobutoxy)quinolin-2(1H)-one 2) of brexpiprazole in 80% isolated yield on a 100 g scale, and different quinolin-2(1H)-one derivatives with various functional groups were demonstrated in 52-89% yields.