2540-09-2

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
7-Chloro-4-methylquinolin-2(1H)-one is utilized as a key compound in pharmaceutical research and drug development due to its demonstrated biological activities and potential therapeutic applications.
Used as an Antimalarial Agent:
In the healthcare industry, 7-chloro-4-methylquinolin-2(1H)-one serves as an antimalarial agent, playing a crucial role in the treatment and prevention of malaria infections.
Used as an Inhibitor of Dopamine Beta-Hydroxylase:
7-Chloro-4-methylquinolin-2(1H)-one is employed as an inhibitor of the enzyme dopamine beta-hydroxylase, which is involved in the conversion of dopamine to norepinephrine. This application is significant in the study and treatment of various neurological conditions.
Used as a Fluorescent Probe for Metal Ion Detection:
7-Chloro-4-methylquinolin-2(1H)-one also functions as a fluorescent probe for the detection of metal ions. This makes it a valuable tool in analytical chemistry and environmental monitoring for the identification and quantification of metal contaminants.

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

Upstream product

• 103906-41-8 (7-chloro-2-hydroxy-[4]quinolyl)-acetic acid 
• 108-42-9 3-chloro-aniline 
• 168554-86-7 5-chloro-2-(1-methylethenyl)benzenamine 
• 823-57-4 2-bromo-5-chloroaniline 
• 124-38-9 carbon dioxide 
• 2415-87-4 3'-chloroacetoacetanilide 
• 110333-96-5 3-oxo-glutaric acid bis-(3-chloro-anilide) 
• 103274-64-2 acetic acid-(2-acetyl-5-chloro-anilide) 

Downstream Products

• 59666-16-9 2,7-dichloro-4-methyl-quinoline 
• 141053-41-0 C₁₈H₁₅ClN₄O₂S 

Relevant academic research and scientific papers

Novel 2-oxoquinoline-6-sulfonamides as thiazide-like diuretics

A series of novel N-aryl-7-chloro-4-methyl-2-oxo-1,2-dihydroquinoline-6- sulfonamides were obtained. The structure-activity relationship (SAR) approach was used to study their diuretic effect on rats. Diuretic activity was exhibited by all the test compounds, with 7-chloro-4-methyl-2-oxo-1,2-dihydroquinoline-6- sulfonanilide being most active. A SAR analysis revealed that the substituted (especially ortho-substituted in the benzene ring) arylamides diminish diuresis compared to the most active compound. For the most and least active compounds, their effects on the electrolyte excretion (Na+, K+, and Cl-) and creatinine level were also studied.

Ru-NHC-Catalyzed Asymmetric Hydrogenation of 2-Quinolones to Chiral 3,4-Dihydro-2-Quinolones

Direct enantioselective hydrogenation of unsaturated compounds to generate chiral three-dimensional motifs is one of the most straightforward and important approaches in synthetic chemistry. We realized the Ru(II)-NHC-catalyzed asymmetric hydrogenation of 2-quinolones under mild reaction conditions. Alkyl-, aryl- and halogen-substituted optically active dihydro-2-quinolones were obtained in high yields with moderate to excellent enantioselectivities. The reaction provides an efficient and atom-economic pathway to construct simple chiral 3,4-dihydro-2-quinolones. The desired products could be further reduced to tetrahydroquinolines and octahydroquinolones.

Synthesis of 2-Quinolinones via a Hypervalent Iodine(III)-Mediated Intramolecular Decarboxylative Heck-Type Reaction at Room Temperature

A hypervalent iodine(III)-mediated intramolecular decarboxylative Heck-type reaction of 2-vinyl-phenyl oxamic acids has been developed. The unique ring-strain-enabled radical decarboxylation mechanism is preliminarily revealed. This protocol features metal-free reaction conditions and operational simplicity, allowing the lactamization of 2-vinylanilines using a readily accessible carbonyl source and the synthesis of various 2-quinolinones with excellent chemoselectivity at room temperature.

Lactamization of sp2C?H Bonds with CO2: Transition-Metal-Free and Redox-Neutral

The first direct use of carbon dioxide in the lactamization of alkenyl and heteroaryl C?H bonds to synthesize important 2-quinolinones and polyheterocycles in moderate to excellent yields is reported. Carbon dioxide, a nontoxic, inexpensive, and readily available greenhouse gas, acts as an ideal carbonyl source. Importantly, this transition-metal-free and redox-neutral process is eco-friendly and desirable for the pharmaceutical industry. Moreover, these reactions feature a broad substrate scope, good functional group tolerance, facile scalability, and easy product derivatization.

Phosphonoalkylquinolin-2-ones as novel antagonists of non-NMDA ionotropic excitatory amino acid receptors

The present invention pertains to antagonists of excitatory amino acid receptors, their method of preparation as well as compositions pertaining to them, which have the general formula: STR1 wherein n is 0, 1, 2, or 3; R 1 and R 2 are selected from the group consisting of hydrogen, halogen, halomethyl, nitro, amino, alkoxy, hydroxyl, hydroxymethyl, C 1 to C 6 lower alkyl and C 7 to C 12 higher alkyl, aryl and aralkyl; and the pharmaceutically acceptable salts thereof.