1220418-77-8

Basic information

• Product Name: 3-Quinolinecarboxylic acid, 6-broMo-, Methyl ester
• Synonyms: 3-Quinolinecarboxylic acid, 6-broMo-, Methyl ester;Methyl 6-broMoquinoline-3-carboxylate
• CAS NO: 1220418-77-8
• Molecular Formula: C₁₁H₈BrNO₂
• Molecular Weight: 266.09072
• Mol File: 1220418-77-8.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 3-Quinolinecarboxylic acid, 6-broMo-, Methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Quinolinecarboxylic acid, 6-broMo-, Methyl ester(1220418-77-8)
• EPA Substance Registry System: 3-Quinolinecarboxylic acid, 6-broMo-, Methyl ester(1220418-77-8)

Safety Data

• Hazardous Substances Data: 1220418-77-8(Hazardous Substances Data)

Usage

General Description

3-Quinolinecarboxylic acid, 6-Bromo-, Methyl ester is a chemical compound with the molecular formula C10H8BrNO2. It is a derivative of quinolinecarboxylic acid with a bromine substituent at the 6 position and a methyl ester group. 3-Quinolinecarboxylic acid, 6-broMo-, Methyl ester is commonly used in the synthesis of pharmaceuticals and agrochemicals due to its potential therapeutic and biological activities. It is also utilized as a building block in organic synthesis to create various other chemical compounds. Additionally, it is known to possess anti-inflammatory and anti-cancer properties, making it a promising candidate for further research and development in the field of medicinal chemistry.

Upstream product

• 50-00-0 formaldehyd 
• 922-67-8 propynoic acid methyl ester 
• 106-40-1 4-bromo-aniline 
• 1001-26-9 ethyl 3-ethoxyacrylate 
• 29124-57-0 2-amino-5-bromobenzaldehyde 
• 67-56-1 methanol 
• 798545-30-9 6-bromoquinoline-3-carboxylic acid 
• 52727-57-8 5-bromo-2-aminobenzoic acid methyl ester 
• 7424-91-1 methyl 3,3-dimethoxypropionate 

Downstream Products

• 1350750-83-2 methyl 6-phenethylquinoline-3-carboxylate 
• 1350750-68-3 methyl 6-(N-(phenylsulfonyl)phenylsulfonamido)quinoline-3-carboxylate 
• 1350750-69-4 6-(phenylsulfonamido)quinoline-3-carboxylic acid 
• 1350750-70-7 6-(phenylsulfonamido)-N-(tetrahydro-2H-pyran-2-yloxy)quinoline-3-carboxamide 
• 1350750-41-2 N-hydroxy-6-[(phenylsulfonyl)amino]quinoline-3-carboxamide 
• 1350750-71-8 methyl 6-(3-phenylureido)quinoline-3-carboxylate 
• 1220418-81-4 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-quinoline-3-carboxylic acid methyl ester 
• 1613219-59-2 6-(4-phenylthiazol-2-yl)-quinoline-3-carboxylic acid 
• 1613220-01-1 6-(4-phenylthiazol-2-yl)-quinoline-3-carboxylic acid methyl ester 
• 1309363-93-6 2-((2-amino-6-o-tolylquinolin-3-yl)methyl)-N-(cyclohexylmethyl) pentanamide 
• 1309364-28-0 2-((2-amino-6-o-tolylquinolin-3-yl)methyl)-N-(cyclohexylmethyl)-3-methylbutanamide 
• 1309364-22-4 2-((2-amino-6-o-tolylquinolin-3-yl)methyl)-N-(cyclohexylmethyl)butanamide 
• 1321991-97-2 (S)-3-(2-amino-6-o-tolylquinolin-3-yl)-N-(cyclohexylmethyl)-2-methylpropanamide 
• 1321991-96-1 (R)-3-(2-amino-6-o-tolylquinolin-3-yl)-N-(cyclohexylmethyl)-2-methylpropanamide 

Relevant articles and documents

Polythiophene-Encapsulated Bimetallic Au-Fe3O4 Nano-Hybrid Materials: A Potential Tandem Photocatalytic System for Nondirected C(sp2)-H Activation for the Synthesis of Quinoline Carboxylates

Hetero-oligophenylene derivative 3 appended with thiophene moieties has been designed and synthesized which undergoes aggregation to form J-type fluorescent aggregates in in H2O/THF (7/3) media. These aggregates served as reactors for the preparation of bimetallic Au-Fe3O4 NPs. During the reduction process, aggregates of derivative 3 were oxidized to the polythiophene species 4. Interestingly, the polythiophene species 4, having a fibrous morphology, served as a shape- and morphology-directed template for assembly of bimetallic Au-Fe3O4 NPs in a flower-like arrangement. Furthermore, polythiophene-encapsulated bimetallic 4:Au-Fe3O4 nanohybrid materials served as an efficient and recyclable catalytic system for C(sp2)-H bond activation of unprotected electron-rich anilines for the construction of synthetically versatile quinoline carboxylates via C-H activation, carbonylation, and subsequent annulation under mild and eco-friendly conditions (aqueous media, room temperature, visible-light irradiation, and aerial conditions).

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).