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Usage

Uses

Used in Pharmaceutical Synthesis:
7-Chloro-2-methyl-4(1H)-quinolinone is used as an intermediate in the pharmaceutical industry for the synthesis of various drugs. Its unique structure and properties allow it to be a key component in the development of new medicinal compounds.
Used in Agrochemical Production:
In the agrochemical sector, 7-chloro-2-methyl-4(1H)-quinolinone serves as an intermediate in the production of different agrochemicals. Its role in this industry is crucial for the creation of effective pesticides and other agricultural chemicals.
Used in Heterocyclic Compound Preparation:
7-Chloro-2-methyl-4(1H)-quinolinone is utilized as a building block for the preparation of various heterocyclic compounds. Its chemical versatility makes it an essential component in the synthesis of complex organic molecules with potential applications in multiple fields.
Used in Medicine:
7-Chloro-2-methyl-4(1H)-quinolinone has potential applications in the field of medicine, where its unique properties can contribute to the development of new therapeutic agents and treatments.
Used in Agriculture:
7-CHLORO-2-METHYL-4(1H)-QUINOLINONE is also used in agriculture, where it plays a role in the development of agrochemicals that can improve crop protection and yield.
Used in Materials Science:
7-Chloro-2-methyl-4(1H)-quinolinone's potential applications extend to materials science, where its properties can be harnessed to create new materials with specific characteristics for various applications.

InChI:InChI=1/C10H8ClNO/c1-6-4-10(13)8-3-2-7(11)5-9(8)12-6/h2-5H,1H3,(H,12,13)

Upstream product

• 108-42-9 3-chloro-aniline 
• 141-97-9 ethyl acetoacetate 
• 63010-73-1 ethyl β-(3-chloroanilino)crotonate 
• 83674-16-2 2-methyl-7-chloro-1,2,3,4-tetrahydroquinolin-4-one 
• 63010-73-1 ethyl 3-(3-chloro)anilino-2-butenoate 

Downstream Products

• 50593-69-6 4,7-dichloro-2-methylquinoline 
• 97892-66-5 2-metil-4-idrazino-7-clorochinolina 
• 1417177-52-6 N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl)-4-chlorobenzenesulfonamide 
• 102374-64-1 4-(7-chloro-2-methylquinolin-4-ylamino)-2-((diethylamino)methyl)phenol 
• 1417177-53-7 N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl)-2,3-dichlorobenzenesulfonamide 
• 1417177-54-8 N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl)-2,4-dichlorobenzenesulfonamide 
• 1446350-07-7 N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl)-2,5-dichlorobenzenesulfonamide 
• 1417177-55-9 N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl)-4-nitrobenzenesulfonamide 
• 1446350-08-8 N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl)-4-cyanobenzenesulfonamide 
• 1446350-10-2 N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl)-3-(trifluoromethyl)benzenesulfonamide 
• 1446350-11-3 N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl)naphthalene-2-sulfonamide 
• 1446350-12-4 N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl) quinoline-8-sulfonamide 
• 1446350-13-5 N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl)-2,4,6-triisopropylbenzenesulfonamide 
• 1446350-14-6 N-(7-chloro-2-methylquinolin-4-yl)-N-(3-((diethylamino)methyl)-4-hydroxyphenyl)-2,4,6-trimethylbenzenesulfonamide 

Relevant academic research and scientific papers

Synthesis of (E)-2-(4,7-dichloroquinolin-2-yl)-3-dimethylamino-2-propene-1-al and its use as a synthetic intermediate

A novel synthesis is described for (E)-2-(4,7-dichloroquinolin-2-yl)-3-dimethylamino-2-propene-1-al (4), which reacts with nucleophiles to yield heterocycle-substituted 4,7-dichloroquinolines (5-7).

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.

Microwave-assisted Synthesis of 2-methyl-4-quinolinones via combes synthesis catalyzed by acidic resin under solvent-free condition

A simple and efficient method for the synthesis of 2-methylquinolin-4(1H)- one derivatives using NKC-9-resin as reusable eco-friendly catalyst via Combes cyclization under solvent-free and microwave irradiation conditions is described. The quinolines were obtained in high yields and in short reaction times.

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.

NaHSO4/SiO2: An efficient catalyst for the synthesis of β-enaminones and 2-methylquinolin-4(1H)-ones under solvent-free condition

An efficient and simplified protocol for NaHSO4/SiO2 catalyzed solvent-free synthesis of β-enaminone and 2-methylquinolin-4(1H)- one derivatives under microwave irradiation is described. A series of functionalized derivatives have been synthesized in shorter reaction times with moderate to good yields. The use of milder catalyst in non-conventional method offers significant advantages over conventional methods, such as higher selectivities, simplicity, solvent-free reaction and non-environmental polluting conditions.

Synthesis of a quinolone library from ynones

A library of 72 quinolones was synthesized from substituted anthranilic acids, using ynone intermediates. These masked β-dicarbonyl synthons allowed cyclization under milder conditions than previously reported quinolone syntheses.

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.