1309365-83-0

Basic information

• Product Name: 6-bromo-2-((4-methoxybenzyl)amino)quinoline-3-carbaldehyde
• Synonyms: 6-bromo-2-((4-methoxybenzyl)amino)quinoline-3-carbaldehyde
• CAS NO: 1309365-83-0
• Molecular Weight: 371.233
• Mol File: 1309365-83-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 6-bromo-2-((4-methoxybenzyl)amino)quinoline-3-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 6-bromo-2-((4-methoxybenzyl)amino)quinoline-3-carbaldehyde(1309365-83-0)
• EPA Substance Registry System: 6-bromo-2-((4-methoxybenzyl)amino)quinoline-3-carbaldehyde(1309365-83-0)

Safety Data

• Hazardous Substances Data: 1309365-83-0(Hazardous Substances Data)

Upstream product

• 103-88-8 4-bromoacetanilide 
• 73568-35-1 6-bromo-2-chloro-3-formylquinoline 
• 2393-23-9 4-methoxy-benzylamine 

Downstream Products

• 1309365-84-1 (E)-methyl 3-(2-(4-methoxybenzylamino)-6-bromoquinolin-3-yl)acrylate 
• 1309365-92-1 (E)-ethyl 3-(2-(4-methoxybenzylamino)-6-bromoquinolin-3-yl)-2-methylacrylate 
• 1309365-85-2 (E)-3-(6-bromo-2-((4-methoxybenzyl)-amino)quinolin-3-yl)acrylic acid 
• 1309365-86-3 (E)-3-(2-(4-methoxybenzylamino)-6-bromoquinolin-3-yl)-N-(cyclohexylmethyl)acrylamide 
• 1309365-87-4 3-(2-(4-methoxybenzylamino)-6-bromoquinolin-3-yl)-N-(cyclohexylmethyl)propanamide 
• 1309365-88-5 3-(2-(4-methoxybenzylamino)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-3-yl)-N-(cyclohexylmethyl)propanamide 
• 1309363-65-2 3-(2-amino-6-(thiazol-4-yl)quinolin-3-yl)-N-(cyclohexylmethyl)propanamide 
• 1309365-89-6 C₃₀H₃₄N₄O₂S 
• 1309365-90-9 3-(2-(4-methoxybenzylamino)-6-(2-chlorophenyl)quinolin-3-yl)-N-(cyclohexylmethyl)propanamide 
• 1309365-91-0 3-(2-(4-methoxybenzylamino)-6-(2-methyl-1H-imidazol-1-yl)quinolin-3-yl)-N-(cyclohexylmethyl)propanamide 
• 1309363-67-4 3-(2-amino-6-(2-methyl-1H-imidazol-1-yl)quinolin-3-yl)-N-(cyclohexylmethyl)propanamide 
• 1309365-93-2 (E)-3-(2-(4-methoxybenzylamino)-6-bromoquinolin-3-yl)-2-methylacrylic acid 
• 1309365-94-3 (E)-3-(2-(4-methoxybenzylamino)-6-bromoquinolin-3-yl)-N-(3,3-dimethylbutyl)-2-methylacrylamide 

Relevant articles and documents

Fragment-Linking Approach Using 19F NMR Spectroscopy to Obtain Highly Potent and Selective Inhibitors of β-Secretase

Fragment-based drug discovery (FBDD) has become a widely used tool in small-molecule drug discovery efforts. One of the most commonly used biophysical methods in detecting weak binding of fragments is nuclear magnetic resonance (NMR) spectroscopy. In part

From fragment screening to in vivo efficacy: Optimization of a series of 2-aminoquinolines as potent inhibitors of beta-site amyloid precursor protein cleaving enzyme 1 (bace1)

Using fragment-based screening of a focused fragment library, 2-aminoquinoline 1 was identified as an initial hit for BACE1. Further SAR development was supported by X-ray structures of BACE1 cocrystallized with various ligands and molecular modeling studies to expedite the discovery of potent compounds. These strategies enabled us to integrate the C-3 side chain on 2-aminoquinoline 1 extending deep into the P2′ binding pocket of BACE1 and enhancing the ligand's potency. We were able to improve the BACE1 potency to subnanomolar range, over 106-fold more potent than the initial hit (900 μM). Further elaboration of the physical properties of the lead compounds to those more consistent with good blood-brain barrier permeability led to inhibitors with greatly improved cellular activity and permeability. Compound 59 showed an IC50 value of 11 nM on BACE1 and cellular activity of 80 nM. This compound was advanced into rat pharmacokinetic and pharmacodynamic studies and demonstrated significant reduction of Aβ levels in cerebrospinal fluid (CSF).