54965-59-2

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Chloro-4-methyl-6-nitro-quinoline serves as an intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with specific therapeutic properties.
Used in Agrochemical Production:
2-Chloro-4-methyl-6-nitro-quinoline is also utilized as an intermediate in the production of agrochemicals, contributing to the creation of effective pesticides and other agricultural products.
Used in Antimicrobial Applications:
2-Chloro-4-methyl-6-nitro-quinoline has been studied for its potential antimicrobial properties, suggesting its use in combating microbial infections.
Used in Antiparasitic Applications:
Research into the compound's antiparasitic properties indicates its potential use in treating parasitic infections, offering a novel approach to parasitic disease management.

InChI:InChI=1/C10H7ClN2O2/c1-6-4-10(11)12-9-3-2-7(13(14)15)5-8(6)9/h2-5H,1H3

Upstream product

• 634-47-9 2-chloro-4-methylquinoline 
• 90771-17-8 4-methyl-6-nitroquinolin-2(1H)-one 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 503-38-8 trichloromethyl chloroformate 
• 607-66-9 4-methylquinolin-2-ol 
• 4835-39-6 N-(4-nitrophenyl)-3-oxobutanamide 
• 857952-45-5 acetic acid-(2-isopropenyl-4-nitro-anilide) 
• 90771-17-8 4-methyl-6-nitro-quinolin-2-ol 

Downstream Products

• 7461-64-5 4-methyl-6-nitro-2-piperidino-quinoline 
• 698392-05-1 4-methyl-6-nitro-2-piperazino-quinoline 
• 859813-77-7 (4-methyl-6-nitro-[2]quinolyl)-(2-morpholino-ethyl)-amine 
• 92853-89-9 (4-chloro-phenyl)-(4-methyl-6-nitro-[2]quinolyl)-amine 
• 90772-83-1 6-amino-2-chloro-4-methylquinoline 
• 855639-85-9 2-hydrazinyl-4-methyl-6-nitroquinoline 
• 31128-02-6 phenyl-(4-methyl-6-nitro-quinolin-2-yl)amine 
• 744220-34-6 N-(2-chloro-4-methylquinolin-6-yl)-2-(4-trifluoromethylphenoxy)acetamide 

Relevant academic research and scientific papers

Novel 8-nitroquinolin-2(1H)-ones as NTR-bioactivated antikinetoplastid molecules: Synthesis, electrochemical and SAR study

To study the antiparasitic 8-nitroquinolin-2(1H)-one pharmacophore, a series of 31 derivatives was synthesized in 1–5 steps and evaluated in vitro against both Leishmania infantum and Trypanosoma brucei brucei. In parallel, the reduction potential of all molecules was measured by cyclic voltammetry. Structure-activity relationships first indicated that antileishmanial activity depends on an intramolecular hydrogen bond (described by X-ray diffraction) between the lactam function and the nitro group, which is responsible for an important shift of the redox potential (+0.3 V in comparison with 8-nitroquinoline). With the assistance of computational chemistry, a set of derivatives presenting a large range of redox potentials (from ?1.1 to ?0.45 V) was designed and provided a list of suitable molecules to be synthesized and tested. This approach highlighted that, in this series, only substrates with a redox potential above ?0.6 V display activity toward L. infantum. Nevertheless, such relation between redox potentials and in vitro antiparasitic activities was not observed in T. b. brucei. Compound 22 is a new hit compound in the series, displaying both antileishmanial and antitrypanosomal activity along with a low cytotoxicity on the human HepG2 cell line. Compound 22 is selectively bioactivated by the type 1 nitroreductases (NTR1) of L. donovani and T. brucei brucei. Moreover, despite being mutagenic in the Ames test, as most of nitroaromatic derivatives, compound 22 was not genotoxic in the comet assay. Preliminary in vitro pharmacokinetic parameters were finally determined and pointed out a good in vitro microsomal stability (half-life > 40 min) and a 92% binding to human albumin.

Identification and optimization of novel 6-acylamino-2-aminoquinolines as potent Hsp90 C-terminal inhibitors

In order to discover novel Hsp90 inhibitors targeting the C-terminal ATP binding pocket, a novobiocin derivative based ROCS model was constructed for virtual screening. Compound 13 was identified as the lead compound and then systematical structure activity relationship (SAR) study was conducted. These efforts led to compound 69, which exhibited potent anti-proliferative activities against MCF7 and SKBr3 breast cancer cell lines. In 4T1 mice breast cancer models, 69 exhibited potent tumor growth inhibition and anti-metastasis effect. Compound 69 as a potent antitumor agent targeting the Hsp90 C-terminal is worthy of further pre-clinical study.

Synthesis and characterization of alkyl and aryl-(4-methyl-6-nitro- quinolin-2-yl)amines: X-ray structures of ethyl and cyclohexyl-(4-methyl-6- nitro-quinolin-2-yl)amine

We have synthesized and characterized a series of alkyl and aryl-(4-methyl-6-nitro-quinolin-2-yl)amines through a high-yield, three-step procedure starting from 4-methylquinolin-2-ol. Nitration using concentrated nitric/sulfuric acids, followed by chlorination in phosphorus oxychloride, yielded 2-chloro-4-methyl-6-nitro-quinoline. All of the intermediates and aminated products have been characterized by multinuclear (1H and 13C) NMR spectroscopy, elemental analysis, and, in the case of the two title compounds (ethyl and cyclohexyl-(4-raethyl-6-nitro-quinolin-2-yl) amine), a single crystal X-ray structure was obtained to verify the nature of the new materials. Copyright Taylor & Francis, Inc.

SUBSTITUTED QUINOLINES AS MCR MODULATORS

Quinolines of formula (I) are useful as MCH mediators, and in the therapy of obesity.

Structure-activity relationships of a novel series of melanin-concentrating hormone (MCH) receptor antagonists

A new series of 2-aminoquinolines has been identified as antagonists of the melanin concentrating hormone receptor (MCH-1R). Syntheses and structure-activity relationships are described leading to a compound having low nanomolar activity against the receptor and demonstrating functional antagonism. Studies also showed that some of the compounds were selective against a range of other G protein-coupled receptors.

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.

PHOTOLYTIC RING-EXPANSIONS OF 4-AZIDOQUINOLINES AND 6-AZIDODIAZINES: SOME UNEXPECTED AZEPINE RING-OPENING REACTIONS

Photolysis of 6-azidoquinazoline in MeOH-KOMe-dioxan yields 8,9-dihydro-5,7-dimethoxy-5H-pyrimidoazepine (5) which on acid hydrolysis ring-opens to the pyrimidine-carbaldehyde (7).The mechanism of formation of this unexpected dimethoxypyrimido-azepine is discussed and related to previous similar results involving 6-azido-2,3-dihydrofuro- and 6-azido-2,3-dihydrothienoquinolines. In contrast, 6-azidoquinoxaline and 6-azido-2-chloro-4-methylquinoline on photolysis under similar conditions undergo ring expansion to the expected pyrazino- and pyridoazepines (22a) and (17) respectively.However, photolysis of the latter azide in MeOH-dioxan yields the 3-(2-pyridyl)propenonitrile derivative (18) in a reaction analogous to that undergone by 6-azidophenazine.