1196155-68-6

Basic information

• Product Name: 3-Quinolinecarboxaldehyde, 6-broMo-
• Synonyms: 3-Quinolinecarboxaldehyde, 6-broMo-;6-broMo-3-Quinolinecarboxaldehyde
• CAS NO: 1196155-68-6
• Molecular Formula: C₁₀H₆BrNO
• Molecular Weight: 236.06474
• EINECS: -0
• Mol File: 1196155-68-6.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 3-Quinolinecarboxaldehyde, 6-broMo-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Quinolinecarboxaldehyde, 6-broMo-(1196155-68-6)
• EPA Substance Registry System: 3-Quinolinecarboxaldehyde, 6-broMo-(1196155-68-6)

Safety Data

• Hazardous Substances Data: 1196155-68-6(Hazardous Substances Data)

Usage

General Description

6-Bromo-3-quinolinecarboxaldehyde is a chemical compound with the molecular formula C10H6BrNO. It is a derivative of quinolinecarboxaldehyde, which is a versatile building block in organic synthesis. The 6-bromo substitution on the quinoline ring makes this compound useful for designing and synthesizing various bioactive molecules and pharmaceuticals. It has been used as a reagent in the synthesis of heterocyclic compounds and as a starting material in the preparation of pharmaceutical intermediates. Additionally, it has shown potential as a fluorescent probe for detecting biomolecules and as an inhibitor for certain enzymes and proteins. Overall, 6-bromo-3-quinolinecarboxaldehyde has important applications in organic chemistry and pharmaceutical research.

Upstream product

• 102-52-3 malonaldehydebis(dimethylacetal) 
• 20357-20-4 5-bromo-2-nitrobenzaldehyde 
• 1220418-77-8 6-bromoquinoline-3-carboxylic acid methyl ester 
• 29124-57-0 2-amino-5-bromobenzaldehyde 
• 52727-57-8 5-bromo-2-aminobenzoic acid methyl ester 
• 1345445-92-2 (6-bromoquinolin-3-yl)methanol 

Downstream Products

• 1297399-18-8 2-(6-bromoquinolin-3-yl)-N-(4-fluorophenyl)-6-(6-nitro-1H-benzo[d]imidazol-2-yl)imidazo[1,2-a]pyridin-3-amine 
• 1297399-19-9 2-(6-bromoquinolin-3-yl)-N-(4-fluorophenyl)-6-(5-(4-fluorophenyl)-1H-imidazol-2-yl)imidazo[1,2-a]pyridin-3-amine 
• 1297399-20-2 2-(6-bromoquinolin-3-yl)-N-(4-fluorophenyl)-6-(5-p-tolyl-1H-imidazol-2-yl)imidazo[1,2-a]pyridin-3-amine 
• 1297399-21-3 2-(6-bromoquinolin-3-yl)-N-(4-fluorophenyl)-6-(5-p-tolyl-1,3,4-oxadiazol-2-yl)imidazo[1,2-a]pyridin-3-amine 
• 1297399-25-7 2-(6-bromoquinolin-3-yl)-N-(4-fluorophenyl)-6-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)imidazo[1,2-a]pyridin-3-amine 
• 1297399-27-9 2-(6-bromoquinolin-3-yl)-N-(4-fluorophenyl)-6-(5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl)imidazo[1,2-a]pyridin-3-amine 
• 1297399-16-6 2-(6-bromoquinolin-3-yl)-N-(4-fluorophenyl)-6-(6-methyl-1H-benzo[d]imidazol-2-yl)imidazo[1,2-a]pyridin-3-amine 
• 1297399-17-7 2-(6-bromoquinolin-3-yl)-6-(6-fluoro-1H-benzo[d]imidazol-2-yl)-N-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-amine 
• 1297399-28-0 2-(6-bromoquinolin-3-yl)-7-fluoro-N-(4-fluorophenyl)imidazo[2,1-b][1,3]benzothiazol-3-amine 
• 1309365-80-7 methyl 3-(6-o-tolylquinolin-3-yl)acrylate 
• 1309365-81-8 N-cyclohexyl-N-methyl-3-(6-o-tolylquinolin-3-yl)propanamide 
• 1309363-64-1 3-(2-amino-6-o-tolylquinolin-3-yl)-N-cyclohexyl-N-methylpropanamide 

Relevant articles and documents

NEW CHEMICAL COMPOUNDS

The present invention encompasses compounds of general formula (1) wherein the groups R1 to R4, Qa, Qb, QH, L and n are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, pharmaceutical preparations which contain such compounds and their use as medicaments.

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).