1810-72-6

Usage

Uses

Used in Polymer Synthesis:
2,6-Dichloroquinoline is used as a monomer in the preparation of poly(quinoline-2,6-diyl) through electrochemical polymerization. This application is significant because the resulting polymers exhibit unique electronic, optical, and electrochemical properties, making them suitable for various applications in the fields of electronics, sensors, and energy storage.
Used in Chemical Research:
As a versatile organic compound, 2,6-dichlorquinoline is also used in chemical research for the synthesis of various quinolines and their derivatives. These derivatives can have potential applications in pharmaceuticals, agrochemicals, and other industries due to their diverse chemical structures and properties.
Used in Pharmaceutical Industry:
2,6-Dichloroquinoline can be utilized as an intermediate in the synthesis of pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications, such as antimalarial, anticancer, and anti-inflammatory agents.
Used in Dye and Pigment Industry:
Due to its color-imparting properties, 2,6-dichlorquinoline can be used in the dye and pigment industry for the production of various colorants. These colorants can be applied in the textile, plastics, and printing industries to impart specific colors to the materials.

Synthesis Reference(s)

The Journal of Organic Chemistry, 67, p. 7884, 2002 DOI: 10.1021/jo016196i

Upstream product

• 1810-67-9 6-chloro-2-hydroxy-quinoline 
• 6563-10-6 6-chloroquinoline N-oxide 
• 19358-40-8 6-chloro-1,2,3,4-tetrahydroquinolin-2-one 
• 612-57-7 6-chloroquinoline 
• 106-47-8 4-chloro-aniline 
• 53691-91-1 N-(4-chlorophenyl)-3-phenylacrylamide 
• 1219101-01-5 bis(6-chloroquinolin-2-yl) disulfide 
• 1810-67-9 6-chloroquinolin-2(1H)-oney 
• 553-03-7 3,4-dihydro-2(1H)-quinolone 
• 79044-04-5 N-(4-Chloro-2-vinyl-phenyl)-acetamide 
• 116035-66-6 N-(4-chloro-2-iodophenyl)acetamide 
• 503-38-8 trichloromethyl chloroformate 

Downstream Products

• 18672-02-1 2-amino-6-chloroquinoline 
• 1810-67-9 6-chloro-2-hydroxy-quinoline 
• 889686-91-3 {2-[(6-chloroquinolin-2-yl)thio]phenyl}methanol 
• 190331-33-0 2-(4-aminophenylthio)-6-chloroquinoline 
• 21335-55-7 n-pentenyl alcohol 
• 78864-94-5 4-[N-(6-chloro-2-quinolinyl)-N-methylamino]phenol 
• 75-18-3 dimethylsulfide 
• 54002-20-9 2,6-di-(methylsulfanyl)quinoline 
• 110131-14-1 C₉H₇NS₂ 
• 107274-76-0 4-(6-chloroquinolin-2-yl)-N,N-dimethylaniline 

Relevant academic research and scientific papers

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.

6-Cyano Analogues of Bedaquiline as Less Lipophilic and Potentially Safer Diarylquinolines for Tuberculosis

Bedaquiline (1) is a new drug for tuberculosis and the first of the diarylquinoline class. It demonstrates excellent efficacy against TB but induces phospholipidosis at high doses, has a long terminal elimination half-life (due to its high lipophilicity), and exhibits potent hERG channel inhibition, resulting in clinical QTc interval prolongation. A number of structural ring A analogues of bedaquiline have been prepared and evaluated for their anti-M.tb activity (MIC90), with a view to their possible application as less lipophilic second generation compounds. It was previously observed that a range of 6-substituted analogues of 1 demonstrated a positive correlation between potency (MIC90) toward M.tb and drug lipophilicity. Contrary to this trend, we discovered, by virtue of a clogP/M.tb score, that a 6-cyano (CN) substituent provides a substantial reduction in lipophilicity with only modest effects on MIC values, suggesting this substituent as a useful tool in the search for effective and safer analogues of 1.

Regioselective Chlorination of Quinoline N-Oxides and Isoquinoline N-Oxides Using PPh3/Cl3CCN

A novel method for the regioselective C2-chlorination of heterocyclic N-oxides has been developed. PPh3/Cl3CCN were used as chlorinating reagents and the desired N-heterocyclic chlorides were obtained smoothly in satisfactory yields. The reactions proceeded in a highly efficient and selective manner across a broad range of substrates demonstrating excellent functional group tolerance. In addition, this chlorination reaction can be used for the modification of N-heterocyclic scaffolds of appealing ligands and pharmaceuticals.

A practical and mild chlorination of fused heterocyclic N-oxides

Fused azine N-oxides were selectively chlorinated at C2 in moderate to excellent yields, employing Vilsmeier reagent as both the activating agent and the nucleophilic chloride source. Remarkable features of the method include simple operation, mild reaction conditions, a wide substrate scope, and the use of only stoichiometric amount of POCl3. The potential extension of this method to a one-pot oxidation/chlorination sequence that obviates the need for isolation of the N-oxide intermediates is also validated.

HIV-1 FUSION INHIBITORS AND METHODS

A new series of HIV-1 fusion inhibitors and methods of use are disclosed. The compounds are based on a substituted indole, benzimidazole, indoline or isoindoline fragment. The compounds find use in inhibiting or preventing HIV fusion from occurring, thus

Development of indole compounds as small molecule fusion inhibitors targeting HIV-1 glycoprotein-41

Nonpeptide inhibition of fusion remains an important goal in anti-HIV research, due to its potential for low cost prophylaxis or prevention of cell-cell transmission of the virus. We report here on a series of indole compounds that have been identified as fusion inhibitors of gp41 through a structure-based drug design approach. Experimental binding affinities of the compounds for the hydrophobic pocket were strongly correlated to fusion inhibitory data (R2 = 0.91), and corresponding inhibition of viral replication confirmed the hydrophobic pocket as a valid target for low molecular weight fusion inhibitors. The most active compound bound to the hydrophobic pocket and inhibited cell-cell fusion and viral replication at submicromolar levels. A common binding mode for the inhibitors in this series was established by carrying out docking studies using structures of gp41 in the Protein Data Bank. The molecules were flexible enough to conform to the contours of the pocket, and the most active compound was able to adopt a structure mimicking the hydrophobic contacts of the D-peptide PIE7. The results enhance our understanding of indole compounds as inhibitors of gp41.

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-

Novel Compounds 679

The invention provides compounds of formula (I), processes for their preparation, pharmaceutical compositions containing them, a process for preparing the pharmaceutical compositions, and their use in therapy, wherein R1, R2, R3

Novel synthesis of 2-chloroquinolines from 2-vinylanilines in nitrile solvent

2-Vinyl- or heteroaryl-substituted anilines were reacted with diphosgene in acetonitrile solution via a reactive imidoyl moiety to afford the corresponding 2-chloroquinolines. Facile syntheses of nine 2-chloroquinoline derivatives from several anilines and their postulate mechanism is described. The postulate mechanism of 2-chloroquinoline formation via imidoyl moiety as a good leaving group shows that the reaction consists of the following three steps: (1) generation of phenylisocyanate, (2) quinoline ring formation, and (3) chlorination on C2 position of quinoline.

II. Synthesis and biological evaluation of some bioisosteres and congeners of the antitumor agent, 2-{4-[(7-chloro-2-quinoxalinyl)oxylphenoxy}propionic acid (XK469)

XK469 (1) is among the most highly and broadly active antitumor agents to have been evaluated in our laboratories. Subsequent developmental studies led to the entry of (R)-(+) 1 (NSC 698215) into phase 1 clinical trials (NIH UO1-CA62487). The antitumor me