71083-61-9

Basic information

• Product Name: 6-chloro-4-oxo-1H-quinoline-3-carbonitrile
• Synonyms: 3-quinolinecarbonitrile, 6-chloro-4-hydroxy-; 6-Chlor-4-hydroxychinolin-3-carbonitril; 6-Chlor-4-oxo-1,4-dihydrochinolin-3-carbonitril; 6-Chloro-4-hydroxyquinoline-3-carbonitrile; 6-chloro-4-oxo-1,4-dihydroquinoline-3-carbonitrile
• CAS NO: 71083-61-9
• Molecular Formula: C₁₀H₅ClN₂O
• Molecular Weight: 204.6125
• Mol File: 71083-61-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 342.3°C at 760 mmHg
• Flash Point: 160.8°C
• Density: 1.46g/cm³
• Vapor Pressure: 7.59E-05mmHg at 25°C
• Refractive Index: 1.658
• CAS DataBase Reference: 6-chloro-4-oxo-1H-quinoline-3-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 6-chloro-4-oxo-1H-quinoline-3-carbonitrile(71083-61-9)
• EPA Substance Registry System: 6-chloro-4-oxo-1H-quinoline-3-carbonitrile(71083-61-9)

Safety Data

• Hazardous Substances Data: 71083-61-9(Hazardous Substances Data)

Usage

General Description

6-chloro-4-oxo-1H-quinoline-3-carbonitrile is a chemical compound with the molecular formula C10H4ClN3O. It is a quinoline derivative with a chlorine atom and a cyano group attached to the third and fourth carbon atoms, respectively. 6-chloro-4-oxo-1H-quinoline-3-carbonitrile is commonly used as a building block in organic synthesis and pharmaceutical development. It has been studied for its potential biological activities, including antimicrobial, anti-inflammatory, and anticancer properties. 6-chloro-4-oxo-1H-quinoline-3-carbonitrile has also been investigated as a precursor for the synthesis of various drug molecules and biologically active compounds.

Upstream product

• 50-00-0 formaldehyd 
• 1257230-31-1 3-(2-bromo-5-chlorophenyl)-3-oxopropanenitrile 
• 106-47-8 4-chloro-aniline 
• 19141-18-5 (Z)-3-p-Chloranilino-2-cyanacrylsaeureethylester 

Relevant articles and documents

Hybrids of Imatinib with Quinoline: Synthesis, Antimyeloproliferative Activity Evaluation, and Molecular Docking

Imatinib (IMT) is the first-in-class BCR-ABL commercial tyrosine kinase inhibitor (TKI). However, the resistance and toxicity associated with the use of IMT highlight the importance of the search for new TKIs. In this context, heterocyclic systems, such as quinoline, which is present as a pharmacophore in the structure of the TKI inhibitor bosutinib (BST), have been widely applied. Thus, this work aimed to obtain new hybrids of imatinib containing quinoline moieties and evaluate them against K562 cells. The compounds were synthesized with a high purity degree. Among the produced molecules, the inhibitor 4-methyl-N3-(4-(pyridin-3-yl)pyrimidin-2-yl)-N1-(quinolin-4-yl)benzene-1,3-diamine (2g) showed a suitable reduction in cell viability, with a CC50 value of 0.9 μM (IMT, CC50 = 0.08 μM). Molecular docking results suggest that the interaction between the most active inhibitor 2g and the BCR-ABL1 enzyme occurs at the bosutinib binding site through a competitive inhibition mechanism. Despite being less potent and selective than IMT, 2g is a suitable prototype for use in the search for new drugs against chronic myeloid leukemia (CML), especially in patients with acquired resistance to IMT.