50593-69-6

Usage

Uses

Used in Pharmaceutical Synthesis:
4,7-Dichloro-2-methylquinoline is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to be chemically modified to create a range of medicinal compounds.
Used in Agrochemical Production:
In the agrochemical industry, 4,7-Dichloro-2-methylquinoline is utilized as a precursor in the development of pesticides and other crop protection agents, contributing to its role in enhancing agricultural productivity.
Used in Antimalarial Applications:
4,7-Dichloro-2-methylquinoline is employed as a potential anti-malarial agent, leveraging its biological activity to combat the malaria parasite, thus offering a new avenue for treatment in affected regions.
Used in Anticancer Research:
As an anti-cancer agent, 4,7-Dichloro-2-methylquinoline is used in research to explore its potential to target and inhibit the growth of cancer cells, offering hope for the development of new therapeutics in oncology.

InChI:InChI=1/C10H7Cl2N/c1-6-4-9(12)8-3-2-7(11)5-10(8)13-6/h2-5H,1H3

Upstream product

• 15644-88-9 7-chloro-4-hydroxy-2-methylquinoline 
• 63010-73-1 ethyl β-(3-chloroanilino)crotonate 
• 1077-74-3 4,7-dichloroquinoline 1-oxide 
• 75-16-1 methylmagnesium bromide 
• 108-42-9 3-chloro-aniline 
• 4965-33-7 2-methyl-7-chloroquinoline 
• 63010-73-1 ethyl 3-(3-chloro)anilino-2-butenoate 
• 4964-78-7 7-chloro-2-methylquinoline 1-oxide 

Downstream Products

• 31432-68-5 4,7-dichloro-2-[2-(5-nitro-furan-2-yl)-vinyl]-quinoline 
• 102374-64-1 4-(7-chloro-2-methylquinolin-4-ylamino)-2-((diethylamino)methyl)phenol 
• 1446350-20-4 N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl)methanesulfonamide 
• 1417177-57-1 N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl)-3,5-dimethylbenzenesulfonamide 
• 1417177-56-0 N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl)-5-chlorothiophene-2-sulfonamide 
• 1446350-19-1 N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl)-2,4-dinitrobenzenesulfonamide 
• 1446350-18-0 N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl) thiophene-2-sulfonamide 
• 1446350-17-9 N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl)-3,4-dichlorobenzenesulfonamide 
• 1446350-16-8 N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl)-3,5-dichlorobenzenesulfonamide 
• 1446350-15-7 N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl)naphthalene-1-sulfonamide 
• 1446350-14-6 N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl)-2,4,6-trimethylbenzenesulfonamide 
• 1446350-13-5 N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl)-2,4,6-triisopropylbenzenesulfonamide 
• 1446350-12-4 N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl) quinoline-8-sulfonamide 
• 1446350-11-3 N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl)naphthalene-2-sulfonamide 

Relevant academic research and scientific papers

Antibacterial activity and fluorescence properties of 4,7-dichloro-2-quinolinemethylacrylate

Currently, some quinoline-based anticancer drugs are successful repurposed for treatment of bacterial infections. This study assessed the antibacterial activity of the new anticancer compound 4,7-dichloro-2-quinolinemethylacrylate (AQM) against bacteria o

Novel, potent, orally bioavailable and selective mycobacterial ATP synthase inhibitors that demonstrated activity against both replicating and non-replicating M. tuberculosis

The mycobacterial F0F1-ATP synthase (ATPase) is a validated target for the development of tuberculosis (TB) therapeutics. Therefore, a series of eighteen novel compounds has been designed, synthesized and evaluated against Mycobacterium smegmatis ATPase. The observed ATPase inhibitory activities (IC50) of these compounds range between 0.36 and 5.45 μM. The lead compound 9d [N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl)-2,3-dichlorobenzenesulfonamide] with null cytotoxicity (CC50 >300 μg/mL) and excellent anti-mycobacterial activity and selectivity (mycobacterium ATPase IC50 = 0.51 μM, mammalian ATPase IC50 >100 μM, and selectivity >200) exhibited a complete growth inhibition of replicating Mycobacterium tuberculosis H37Rv at 3.12 μg/mL. In addition, it also exhibited bactericidal effect (approximately 2.4 log10 reductions in CFU) in the hypoxic culture of non-replicating M. tuberculosis at 100 μg/mL (32-fold of its MIC) as compared to positive control isoniazid [approximately 0.2 log10 reduction in CFU at 5 μg/mL (50-fold of its MIC)]. The pharmacokinetics of 9d after p.o. and IV administration in male Sprague-Dawley rats indicated its quick absorption, distribution and slow elimination. It exhibited a high volume of distribution (Vss, 0.41 L/kg), moderate clearance (0.06 L/h/kg), long half-life (4.2 h) and low absolute bioavailability (1.72%). In the murine model system of chronic TB, 9d showed 2.12 log10 reductions in CFU in both lung and spleen at 173 μmol/kg dose as compared to the growth of untreated control group of Balb/C male mice infected with replicating M. tuberculosis H37Rv. The in vivo efficacy of 9d is at least double of the control drug ethambutol. These results suggest 9d as a promising candidate molecule for further preclinical evaluation against resistant TB strains.

Direct, catalytic, and regioselective synthesis of 2-alkyl-, aryl-, and alkenyl-substituted N -Heterocycles from n -oxides

A one-step transformation of heterocyclic N-oxides to 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles is described. The success of this broad-scope methodology hinges on the combination of copper catalysis and activation by lithium fluoride or magnesium chloride. The utility of this method for the late-stage modification of complex N-heterocycles is exemplified by facile syntheses of new structural analogues of several antimalarial, antimicrobial, and fungicidal agents.

N-(3-((DIETHYLAMINO) METHYL)-4-HYDROXYPHENYL)-N-(QUINOLIN-4-YL) SULFONAMIDES FOR THE TREATMENT OF TUBERCULOSIS AND PROCESS OF PREPARATION THEREOF

The present invention relates to novel N-(3-((diethylamino)methyl)-4-hydroxyphenyl)-N-(quinolin-4- yl)sulfonamide derivatives, their preparation, to pharmaceutical compositions comprising them, and to their use as therapeutic agents, particularly in the prevention or treatment of tuberculosis. The present invention particularly relates to compounds of formula A[Formula I]: wherein: R = methyl, (or) R = a group of the structure [Formula II] wherein, R1, R2, and R3 may be same or different present at any position(s) and are groups selected from the group consisting of hydrogen, halogen, alkyl (C1-C3), nitro, cyano, trifluoromethyl, (or) R is a group of the structure [Formula III] wherein X may be CH or N, and the attachment point of sulfonyl may be at the position 1 or 2, (or) R is a group of the structure [Formula IV] Where R1 is hydrogen or halogen, (or) R is a group of the structure. [Formula V]

N1-{4-[(10S)-Dihydroartemisinin-10-oxyl]}phenylmethylene-N 2-(2-methylquinoline-4-yl)hydrazine derivatives as antiplasmodial falcipain-2 inhibitors

A series of N1-{4-[(10S)-dihydroartemisinin- 10-oxyl]}phenylmethylene-N2-(2-methylquinoline-4-yl) hydrazine derivatives 9a-9n possessing 4-quinolylhydrazone and artemisinin cores were herein synthesized and evaluated for their activities against cysteine protease falcipain- 2 of Plasmodium falciparum. The structures were clearly confirmed by elemental analysis, 1H NMR, and mass spectra. The pharmacological results indicated that all compounds showed excellent activity against recombinant falcipain-2 (IC50 = 0.15-2.28 μM). The best one of this series was compound 9d (IC50 = 0.15 μM). The molecular docking results showed that the compound 9d made close contact with the key active site of cysteine protease falcipain-2.

ANTIMICROBIAL COMPOUNDS BASED UPON 4-AMINOQUINOLINE

There is provided compounds of formula I wherein R1, R2, R3, R4, X1, X2 and A have meanings given in the description. Also provided are medical uses of such compounds, such as the killing c

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.