607377-99-1

Basic information

• Product Name: 2-chloroquinolin-5-amine
• Synonyms: 2-chloroquinolin-5-amine
• CAS NO: 607377-99-1
• Molecular Formula: C₉H₇ClN₂
• Molecular Weight: 178.61828
• Mol File: 607377-99-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-chloroquinolin-5-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloroquinolin-5-amine(607377-99-1)
• EPA Substance Registry System: 2-chloroquinolin-5-amine(607377-99-1)

Safety Data

• Hazardous Substances Data: 607377-99-1(Hazardous Substances Data)

Usage

Description

2-Chloroquinolin-5-amine is a chemical compound with the molecular formula C9H7ClN2, belonging to the quinoline family and featuring a chlorine atom and an amine group. It is a white to light yellow solid that is sparingly soluble in water but more soluble in organic solvents. Due to its potential harmful effects if ingested, inhaled, or in contact with the skin, appropriate safety measures should be taken when handling this compound.

Uses

Used in Pharmaceutical Industry:
2-Chloroquinolin-5-amine is utilized as an intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs due to its unique chemical structure and properties.
Used in Agrochemical Industry:
2-chloroquinolin-5-amine also serves as an intermediate in the production of agrochemicals, playing a role in the creation of substances that help protect crops and enhance agricultural productivity.
Used in Dye Industry:
2-Chloroquinolin-5-amine is employed in the synthesis of dyes, where its chemical properties contribute to the color and stability of the final products.
Used in Drug Development:
Furthermore, 2-chloroquinolin-5-amine has been studied for its potential as a building block in the development of new drugs, indicating its versatility and importance in medicinal chemistry.

Upstream product

• 6938-27-8 5-nitro-2<1H>quinolinone 
• 1001184-83-3 tert-butyl (1-oxidoquinolin-5-yl)carbamate 
• 161604-57-5 tert-butyl quinolin-5-ylcarbamate 
• 611-34-7 5-Aminoquinoline 
• 13067-94-2 2-chloro-5-nitroquinoline 
• 7439-89-6 iron 

Downstream Products

• 1016315-15-3 N-(2-Chloro-quinolin-5-yl)-4-fluoro-benzenesulfonamide 

Relevant articles and documents

Synthesis and structure-activity relationships of quinolinone and quinoline-based P2X7 receptor antagonists and their anti-sphere formation activities in glioblastoma cells

Screening a compound library of quinolinone derivatives identified compound 11a as a new P2X7 receptor antagonist. To optimize its activity, we assessed structure-activity relationships (SAR) at three different positions, R1, R2 and R3, of the quinolinone scaffold. SAR analysis suggested that a carboxylic acid ethyl ester group at the R1 position, an adamantyl carboxamide group at R2 and a 4-methoxy substitution at the R3 position are the best substituents for the antagonism of P2X7R activity. However, because most of the quinolinone derivatives showed low inhibitory effects in an IL-1β ELISA assay, the core structure was further modified to a quinoline skeleton with chloride or substituted phenyl groups. The optimized antagonists with the quinoline scaffold included 2-chloro-5-adamantyl-quinoline derivative (16c) and 2-(4-hydroxymethylphenyl)-5-adamantyl-quinoline derivative (17k), with IC50 values of 4 and 3 nM, respectively. In contrast to the quinolinone derivatives, the antagonistic effects of the quinoline compounds (16c and 17k) were paralleled by their ability to inhibit the release of the pro-inflammatory cytokine, IL-1β from LPS/IFN-γ/BzATP-stimulated THP-1 cells (IC50 of 7 and 12 nM, respectively). In addition, potent P2X7R antagonists significantly inhibited the sphere size of TS15-88 glioblastoma cells.

IMAGING THE CENTRAL NERVOUS SYSTEM

The present invention provides novel compounds which may be used as in vivo imaging agents. The compounds of the invention are useful in a method to image the expression of P2X7 receptors in a subject, as a means to facilitate the diagnosis of a range of disease states.

QUINOLINES

The present invention relates to 2-Aminoquinoline derivatives of general formula I and pharmaceutically-acceptable acid-addition salts thereof, wherein R1, R2 and X are as defined in the specification. The compounds may be used as 5-