28615-67-0

Basic information

• Product Name: 4-CHLOROQINOLINE-2-CARBOXALDEHYDE
• Synonyms: 4-CHLOROQINOLINE-2-CARBOXALDEHYDE;4-Chloroquinoline-2-carboxaldehyde;4-chloroquinoline-2-carbaldehyde;2-Quinolinecarboxaldehyde,4-chloro-
• CAS NO: 28615-67-0
• Molecular Formula: C₁₀H₆ClNO
• Molecular Weight: 191.616
• Mol File: 28615-67-0.mol
• Article Data: 11

Chemical Properties

• Melting Point: 231 °C(Solv: ethanol (64-17-5); chloroform (67-66-3))
• Boiling Point: 325.2 °C at 760 mmHg
• Flash Point: 150.5 °C
• Appearance: /
• Density: 1.364 g/cm³
• Vapor Pressure: 0.000234mmHg at 25°C
• Refractive Index: 1.692
• PKA: 2.22±0.50(Predicted)
• CAS DataBase Reference: 4-CHLOROQINOLINE-2-CARBOXALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLOROQINOLINE-2-CARBOXALDEHYDE(28615-67-0)
• EPA Substance Registry System: 4-CHLOROQINOLINE-2-CARBOXALDEHYDE(28615-67-0)

Safety Data

• Hazardous Substances Data: 28615-67-0(Hazardous Substances Data)

Usage

General Description

4-Chloroquinoline-2-carboxaldehyde is a chemical compound that is commonly used in the pharmaceutical industry. It is a derivative of quinoline and contains a chlorine atom and an aldehyde functional group. 4-CHLOROQINOLINE-2-CARBOXALDEHYDE is important in the synthesis of various drugs and pharmaceuticals, as it can be used as a starting material for the production of other chemical compounds. It is also known for its antimicrobial and antiparasitic properties, and is used in the development of medications to treat infections and diseases. Additionally, 4-chloroquinoline-2-carboxaldehyde has applications in the field of organic synthesis and can be used as a reagent in chemical reactions to produce a wide range of different products.

InChI:InChI=1/C10H6ClNO/c11-9-5-7(6-13)12-10-4-2-1-3-8(9)10/h1-6H

Upstream product

• 4295-06-1 4-chloro-2-methylquinoline 
• 67-56-1 methanol 
• 611-35-8 4-chloroquinoline 
• 607-67-0 4-hydroxy-2-methylquinoline 
• 20461-86-3 2,2-diethoxy acetic acid 

Downstream Products

• 15733-82-1 2-carboxy-4-chloroquinoline 

Relevant articles and documents

Metal- and Acid-Free C-H Formylation of Nitrogen Heterocycles: Using Trioxane as an Aldehyde Equivalent Enabled by an Organic-Soluble Oxidant

A metal-free, innate, and practical C-H formylation of nitrogen heterocycles using trioxane as a formyl equivalent is reported. This reaction provides a mild and robust method for modifying medicinally relevant heterocycles with an aldehyde handle. The use of an organic soluble oxidant, tetrabutylammonium persulfate, is critical in promoting the desired coupling.

Discovery of 4-anilinoquinolinylchalcone derivatives as potential NRF2 activators

Activation of nuclear factor erythroid-2-related factor 2 (NRF2) has been proven to be an effective means to prevent the development of cancer, and natural curcumin stands out as a potent NRF2 activator and cancer chemopreventive agent. In this study, we have synthesized a series of 4-anilinoquinolinylchalcone derivatives, and used a NRF2 promoter-driven firefly luciferase reporter stable cell line, the HaCaT/ARE cells, to screen a panel of these compounds. Among them, (E)-3-{4-[(4-acetylphenyl)amino]quinolin-2-yl}-1-(4-fluorophenyl)prop-2-en-1-one (13b) significantly increased NRF2 activity in the HaCaT cell with a half maximal effective concentration (EC50) value of 1.95 μM. Treatment of compound 13b upregulated HaCaT cell NRF2 expression at the protein level. Moreover, the mRNA level of NRF2 target genes, heme oxygenase-1 (HO-1), glutamate-cysteine ligase catalytic subunit (GCLC), and glucose-6-phosphate dehydrogenase (G6PD) were significantly increased in HaCaT cells upon the compound 13b treatment. The molecular docking results exhibited that the small molecule 13b is well accommodated by the bound region of Kelch-like ECH-associated protein 1 (Keap1)-Kelch and NRF2 through stable hydrogen bonds and hydrophobic interaction, which contributed to the enhancement of affinity and stability between the ligand and receptor. Compound 13b has been identified as the lead compound for further structural optimization.

Endeavors towards transformation of M. tuberculosis thymidylate kinase (MtbTMPK) inhibitors into potential antimycobacterial agents

As the last enzyme in nucleotide synthesis as precursors for DNA replication, thymidylate kinase of M. tuberculosis (MtbTMPK) attracts significant interest as a target in the discovery of new anti-tuberculosis agents. Earlier, we discovered potent MtbTMPK inhibitors, but these generally suffered from poor antimycobacterial activity, which we hypothesize is due to poor bacterial uptake. To address this, we herein describe our efforts to equip previously reported MtbTMPK inhibitors with targeting moieties to increase the whole cell activity of the hybrid analogues. Introduction of a simplified Fe-chelating siderophore motif gave rise to analogue 17 that combined favorable enzyme inhibitory activity with significant activity against M. tuberculosis (MIC of 12.5 μM). Conjugation of MtbTMPK inhibitors with an imidazo[1,2-a]pyridine or 3,5-dinitrobenzamide scaffold afforded analogues 26, 27 and 28, with moderate MtbTMPK enzyme inhibitory potency, but sub-micromolar activity against mycobacteria without significant cytotoxicity. These results indicate that conjugation with structural motifs known to favor mycobacterial uptake may be a valid approach for discovering new antimycobacterial agents.