56824-90-9

Basic information

• Product Name: ETHYL 4-CHLORO-8-FLUOROQUINOLINE-3-CARBOXYLATE
• Synonyms: 4-Chloro-8-fluoroquinoline-3-carboxylic acid ethyl ester
• CAS NO: 56824-90-9
• Molecular Formula: C₁₂H₉ClFNO₂
• Molecular Weight: 253.6568
• Mol File: 56824-90-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 332.1 °C at 760 mmHg
• Flash Point: 154.6 °C
• Appearance: /
• Density: 1.354 g/cm³
• Vapor Pressure: 0.00015mmHg at 25°C
• Refractive Index: 1.593
• Storage Temp.: 2-8°C
• CAS DataBase Reference: ETHYL 4-CHLORO-8-FLUOROQUINOLINE-3-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 4-CHLORO-8-FLUOROQUINOLINE-3-CARBOXYLATE(56824-90-9)
• EPA Substance Registry System: ETHYL 4-CHLORO-8-FLUOROQUINOLINE-3-CARBOXYLATE(56824-90-9)

Safety Data

• Hazardous Substances Data: 56824-90-9(Hazardous Substances Data)

Usage

Description

Ethyl 4-chloro-8-fluoroquinoline-3-carboxylate is an organic compound that serves as a crucial intermediate in the synthesis of various quinoline-based molecules. It is characterized by its unique chemical structure, which includes a chlorine atom at the 4th position and a fluorine atom at the 8th position of the quinoline ring. Ethyl 4-chloro-8-fluoroquinoline-3-carboxylate plays a significant role in the development of pharmaceuticals and other chemical applications due to its versatile reactivity and functional group compatibility.

Uses

Used in Pharmaceutical Industry:
Ethyl 4-chloro-8-fluoroquinoline-3-carboxylate is used as a key intermediate for the synthesis of [[(alkylsulfonyl)phenoxy]phenyl]quinolines. These quinoline derivatives exhibit good binding affinity for the liver X receptor beta (LXRβ), which plays a crucial role in regulating lipid and glucose metabolism, inflammation, and cellular proliferation. The moderate binding selectivity over liver X receptor alpha (LXRα) makes these compounds potentially useful in the treatment of various diseases, including metabolic disorders, atherosclerosis, and neurodegenerative diseases.
Additionally, the compound may be utilized in other industries for different applications, such as:
1. Chemical Research and Development:
Ethyl 4-chloro-8-fluoroquinoline-3-carboxylate can be used as a starting material or building block in the synthesis of novel quinoline-based compounds with potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.
2. Drug Design and Optimization:
Ethyl 4-chloro-8-fluoroquinoline-3-carboxylate can be employed in the design and optimization of new drug candidates targeting LXRβ, which may lead to the development of more effective and selective therapies for diseases associated with this receptor.
3. Academic and Industrial Research:
Ethyl 4-chloro-8-fluoroquinoline-3-carboxylate can be used in research laboratories for studying the structure-activity relationships of quinoline-based compounds and exploring their potential applications in various fields.

InChI:InChI=1/C12H9ClFNO2/c1-2-17-12(16)8-6-15-11-7(10(8)13)4-3-5-9(11)14/h3-6H,2H2,1H3

Upstream product

• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 63010-68-4 diethyl [(2-fluoroanilino)methylidene]malonate 
• 348-54-9 2-Fluoroaniline 
• 63010-69-5 ethyl 8-fluoro-4-hydroxy-3-quinolinecarboxylate 

Downstream Products

• 1207711-34-9 C₁₈H₁₄FNO₃ 
• 702706-01-2 3-(6-Fluoro-3-oxo-3,5-dihydro-pyrazolo[4,3-c]quinolin-2-yl)-benzoic acid 

Relevant articles and documents

Synthesis and screening of triazolopyrimidine scaffold as multi-functional agents for Alzheimer's disease therapies

In present study a series of triazolopyrimidine-quinoline and cyanopyridine-quinoline hybrids were designed, synthesized and evaluated as acetylcholinesterase inhibitors (AChEIs). Molecular docking and scoring was utilized for the design of inhibitors. The molecules were synthesized via an easily accessible, convergent synthetic route. Three triazolopyrimidine based compounds showed nanomolar activity towards acetylcholinesterase. Among them, Ethyl 6-fluoro-4-(4-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)piperazin-1-yl)quinoline-3-carboxylate (10d), strongly inhibited AChE with IC50 value of 42 nM. Furthermore compound 10d was identified as most promising compound with 12 fold selectivity against butyrylcholinesterase (BuChE). This compound displayed a composed multitargeted profile with promising inhibition of self-induced and AChE - induced Aβ aggregation and antioxidant activity.

QUINOLINE DERIVATIVES AS CASPASE-3 INHIBITOR, PREPARATION PROCESS FOR THE SAME AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

Provided is a quinoline derivative represented by the following Formula (1) for use in treating a caspase- mediated disease by inhibition of caspase-3 activity. Further provided are a method for preparing the quinoline derivative or a pharmaceutically acceptable salt thereof and a pharmaceutical composition containing the same.