406204-90-8

Basic information

• Product Name: 6-bromo-2,4-dichloroquinoline
• Synonyms: 6-bromo-2,4-dichloroquinoline
• CAS NO: 406204-90-8
• Molecular Formula: C₉H₄BrCl₂N
• Molecular Weight: 276.94476
• Mol File: 406204-90-8.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 342.2±37.0 °C(Predicted)
• Appearance: /
• Density: 1.765±0.06 g/cm3(Predicted)
• PKA: -1.93±0.50(Predicted)
• CAS DataBase Reference: 6-bromo-2,4-dichloroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6-bromo-2,4-dichloroquinoline(406204-90-8)
• EPA Substance Registry System: 6-bromo-2,4-dichloroquinoline(406204-90-8)

Safety Data

• Hazardous Substances Data: 406204-90-8(Hazardous Substances Data)

Usage

General Description

6-Bromo-2,4-dichloroquinoline is a synthetic chemical compound that belongs to the quinoline family. It is a derivative of quinoline and is characterized by the presence of a bromine atom on the sixth carbon and two chlorine atoms on the second and fourth carbon on the quinoline ring. 6-bromo-2,4-dichloroquinoline is widely used in the field of organic synthesis and medicinal chemistry for the development of novel pharmaceuticals and agrochemicals. It possesses unique chemical properties that make it valuable for various research and industrial applications, including as a building block for the synthesis of more complex organic compounds. The compound's structure and reactivity make it a versatile intermediate in the production of pharmaceuticals and other important chemicals.

Upstream product

• 141-82-2 malonic acid 
• 106-40-1 4-bromo-aniline 
• 54675-23-9 6-bromo-4-hydroxyquinoline-2(1H)-one 
• 95262-09-2 3-[(4-bromophenyl)amino]-3-oxopropanoic acid 
• 669000-20-8 methyl 3-((4-bromophenyl)amino)-3-oxopropanoate 
• 138964-51-9 6-bromoquinoline-2,4(1H, 3H)-dione 
• 2033-24-1 cycl-isopropylidene malonate 
• 2254506-51-7 6-bromo-2-hydroxyquinolin-4(1H)-one 

Downstream Products

• 1386328-69-3 ethyl 4-(3-(6-bromo-2-chloroquinolin-4-yloxy) phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 1599529-43-7 4-((6-bromo-4-chloro-2-methoxyquinolin-3-yl)methyl)benzonitrile 
• 1599529-42-6 4-((6-bromo-2,4-dichloroquinolin-3-yl)methyl)benzonitrile 
• 1424371-22-1 dimethyl 4-(4-(6-bromo-2-chloroquinolin-4-yloxy)phenyl)-2,6-dimethyl-1,4-dihydro pyridine-3,5-dicarboxylate 
• 1424371-12-9 diethyl 4-(4-(6-bromo-2-chloroquinolin-4-yloxy)phenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 

Relevant articles and documents

Design and synthesis of novel conformationally constrained 7,12-dihydrodibenzo[b,h][1,6] naphthyridine and 7H-Chromeno[3,2-c] quinoline derivatives as topoisomerase I inhibitors: In vitro screening, molecular docking and ADME predictions

Novel non-camptothecin (non-CPT) class of conformationally constrained, hitherto unknown 7,12-dihydrodibenzo[b,h][1,6] naphthyridine and 7H-Chromeno[3,2-c] quinoline derivatives have been designed, synthesized and evaluated for anti-cancer activity. In vi

Novel Pyrazoloquinolin-2-ones: Design, synthesis, docking studies, and biological evaluation as antiproliferative EGFR-TK inhibitors

Two new series of diethyl 2-[2-(substituted-2-oxo-1,2-dihydroquinolin-4-yl)hydrazono]-succinates 6a-g and 1-(2-oxo-1,2-dihydroquinolin-4-yl)-1H-pyrazoles 7a-f have been designed and synthesized. The structures of the synthesized compounds were proved by IR, mass, NMR (2D) spectra and elemental analyses. The target compounds were evaluated for their in vitro cytotoxic activity against 60 cancer cell lines according to NCI protocol. Consequently, seven compounds were further examined against the most sensitive cell lines, leukemia CCRF-CEM, and MOLT-4. 5-Amino-1-(6-bromo-2-oxo-1,2-dihydroquinolin-4-yl)-1H-pyrazole-3,4-dicarbonitrile (7f) was the most active product, with IC50 = 1.35 uM and 2.42 uM against MOLT-4 and CCRF-CEM, respectively. Also, it showed a remarkable inhibitory activity compared to erlotinib on the EGFR TK with IC50 = 247.14 nM and 208.42 nM, respectively. Cell cycle analysis of MOLT-4 cells treated with 7f showed cell cycle arrest at G2/M phase (supported by Caspases, BAX and Bcl-2 studies) with a significant pro-apoptotic activity as indicated by annexin V-FITC staining. Moreover, the docking study indicated that both the pyrazole moiety and the quinolin-2-one ring showed good fitting into EGFR (PDB code: 1M17). In order to interpret SAR of the designed compounds, and provide a basis for further optimization, molecular docking of the synthesized compounds to known EGFR inhibitors was performed. The study illustrated the effect of several factors on the compounds’ activity.

Identification and structure activity relationships of quinoline tertiary alcohol modulators of RORγt

A high-throughput screen of the ligand binding domain of the nuclear receptor retinoic acid-related orphan receptor gamma t (RORγt) employing a thermal shift assay yielded a quinoline tertiary alcohol hit. Optimization of the 2-, 3- and 4-positions of the quinoline core using structure-activity relationships and structure-based drug design methods led to the discovery of a series of modulators with improved RORγt inhibitory potency and inverse agonism properties.