4203-18-3

Usage

Uses

4,6-dichloroquinoline is a useful research chemical.

Chemical Properties

Yellow solid

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 1264, 1946 DOI: 10.1021/ja01211a038

InChI:InChI=1/C9H5Cl2N/c10-6-1-2-9-7(5-6)8(11)3-4-12-9/h1-5H

Upstream product

• 6563-10-6 6-chloroquinoline N-oxide 
• 23432-43-1 6-chloro-4-hydroxyquinoline 
• 25063-46-1 5-(((4-chlorophenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 35973-14-9 6-chloro-4-hydroxy-3-quinoline carboxylic acid 
• 70271-77-1 6-chloro-4-hydroxyquinoline-3-carboxylic acid ethyl ester 
• 19056-79-2 diethyl 4-chloroanilinomethylenemalonate 
• 106-47-8 4-chloro-aniline 
• 612-57-7 6-chloroquinoline 
• 21921-70-0 6-chloroquinolin-4(1H)-one 
• 79607-22-0 6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester 
• 53977-19-8 6-chloro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid 

Downstream Products

• 133325-73-2 6-chloro-4-p-tolylmercapto-quinoline 
• 857439-65-7 N-(6-chloro-[4]quinolyl)-o-phenylenediamine 
• 20028-60-8 6-Chlor-4-amino-chinolin 
• 749916-89-0 4-chloro-6-(4-tolyl)quinoline 
• 676262-10-5 6-chloro-4-methoxyquinoline 
• 103914-57-4 4,6-dichloro-2-(4-fluorophenyl)quinoline 
• 75-18-3 dimethylsulfide 
• 1219100-98-7 4,6-di-(methylsulfanyl)quinoline 
• 1020150-09-7 N-[4-(2-amino-6-methylpyrimidin-4-ylamino)phenyl]-4-(6-chloroquinolin-4-ylamino)benzamide 
• 1082748-39-7 C₉H₈ClN₃ 
• 1621082-97-0 N-(4-chloro-2-{1-[(4-methylphenyl)sulfonyl]-1H-pyrazol-3-yl}phenyl)-4-methylbenzenesulfonamide 
• 1621083-01-9 N-{4-chloro-2-[1-(phenylsulfonyl)-1H-pyrazol-3-yl]phenyl}benzenesulfonamide 

Relevant academic research and scientific papers

A Selective and Orally Bioavailable Quinoline-6-Carbonitrile-Based Inhibitor of CDK8/19 Mediator Kinase with Tumor-Enriched Pharmacokinetics

Senexins are potent and selective quinazoline inhibitors of CDK8/19 Mediator kinases. To improve their potency and metabolic stability, quinoline-based derivatives were designed through a structure-guided strategy based on the simulated drug–target dockin

Development of novel quinoline-based sulfonamides as selective cancer-associated carbonic anhydrase isoform ix inhibitors

A new series of quinoline-based benzenesulfonamides (QBS) were developed as potential carbonic anhydrase inhibitors (CAIs). The target QBS CAIs is based on the 4-anilinoquinoline scaffold where the primary sulphonamide functionality was grafted at C4 of t

QUINOLINE-BASED COMPOUNDS AND METHODS OF INHIBITING CDK8/19

Disclosed herein are quinoline-based compounds and method for inhibiting CDK8 or CDK19 for the intervention in diseases, disorders, and conditions. The quinoline-based composition comprise substituents at quinoline ring positions 4 and 6, wherein the substituent at position 4 is selected from a substituted or unsubstituted arylalkylamine or a substituted or unsubstituted arylhetrocyclylamine. Pharmaceutical compositions comprising the substituted qunioline compositions, methods of inhibiting CDK8 or CDK19, and methods of treating CDK8/19-associated diseases, disorders, or conditions are also disclosed.

Synthesis, molecular docking study, and evaluation of the antiproliferative action of a new group of propargylthio- and propargylselenoquinolines

This study describes the synthesis of a new group of halogenopropargylthio- , dipropargylthio-, and halogenopropargylseleno-quinoline derivatives. The ability of all of the synthesized compounds to inhibit the proliferation of the T-47D, MCF-7, MDA-MB-231, and SNB-19 cell lines was determined with the WST-1 assay. The normal fibroblast cell line (HFF-1) was used as a control. The cytotoxic properties of these new, modified propargylquinoline derivatives were comparable to those of cisplatin. The most active compounds, 4,7-dipropargylthiquinoline (8b) and 7-chloro-4-propargylselenoquinoline (5b), were docked into the binding site of human CYP1A1 and CYP1B1. Our data indicate that these derivatives may present promising chemotherapeutic agents, possibly targeting CYP1s pathway.

Synthesis and in vitro evaluation of new benzenesulfonamides as antileishmanial agents

This paper describes the synthesis and the antileishmanial activity of new pyrazolyl benzenesulfonamide derivatives. These were elucidated by spectrometric methods. Some compounds showed a significant in vitro activity against Leishmania amazonensis, highlighting the derivative 1e. These pyrazolyl benzenesulfonamide derivatives did not show any toxicity in murine macrophage.

Structural optimization of quinolon-4(1 H)-imines as dual-stage antimalarials: Toward increased potency and metabolic stability

Discovery of novel effective and safe antimalarials has been traditionally focused on targeting erythrocytic parasite stages that cause clinical symptoms. However, elimination of malaria parasites from the human population will be facilitated by intervent

From 2,3-, 2,6-, 3,4- and 4,6-dichloroquinolines to isomeric chloroquinolinesulfonyl chlorides

The action of sodium methanethiolate (in boiling DMF) on x,y-dichloroquinolines (1) (x=3 or 6, y=2 or 4) occured via chlorine ipso-substitution followed by methanethiolato-S-demethylation to yield x,y-quinolinedithiolates 2A which were: i) subjected to S-

QUINOLINE DERIVATIVES FOR MODULATING DNA METHYLATION

Quinoline derivatives, particularly 4-anilinoquinoline derivatives, are provided. Such quinoline derivatives can be used for modulation of DNA methylation, such as effective inhibition of methylation of cytosine at the C-5 position, for example via selective inhibition of DNA methyltransferase DNMT1. Methods for synthesizing numerous 4-anilinoquinoline derivatives and for modulating DNA methylation are provided. Also provided are methods for formulating and administering these compounds or compositions to treat conditions such as cancer and hematological disorders.

Synthesis of ring-substituted 4-aminoquinolines and evaluation of their antimalarial activities

A simple two-step synthesis method was used to make 51 B-ring-substituted 4-hydroxyquinolines allowing analysis of the effect of ring substitutions on inhibition of growth of chloroquine sensitive and resistant strains of Plasmodium falciparum, the dominant cause of malaria morbidity. Substituted quinoline rings other than the 7-chloroquinoline ring found in chloroquine were found to have significant activity against the drug-resistant strain of P. falciparum W2.

Antimalarials: Synthesis of 4-aminoquinolines that circumvent drug resistance in malaria parasites

The strategies described here have permitted the synthesis of a series of 4-aminoquinoline antimalarials. Substantive improvements over previous syntheses include nucleophilic substitution with neat amine rather than in phenol, regioselective reductive alkylation to convert the terminal primary amine (12a-20a) on the diaminoalkane side chain to a diethylamino group, and purification by column chromatography with basic alumina. The 1H nmr spectra obtained after regioselective reductive alkylation with sodium borodeuteride (in comparison with sodium borohydride) demonstrated that this reductive alkylation proceeds via formation and subsequent reduction of the corresponding diamides in situ.