50593-73-2

Usage

Uses

Used in Pharmaceutical Industry:
4-CHLORO-6-METHOXY-2-METHYLQUINOLINE is used as a building block for the synthesis of various drugs and biologically active molecules due to its unique structure and functional groups. It plays a crucial role in the development of new pharmaceuticals and organic compounds.
Used in Medicinal Chemistry Research:
4-CHLORO-6-METHOXY-2-METHYLQUINOLINE is used as a target for further research in medicinal chemistry, given its potential biological activities. Its exploration may lead to the discovery of new therapeutic agents and contribute to the advancement of the pharmaceutical field.

InChI:InChI=1/C11H10ClNO/c1-7-5-10(12)9-6-8(14-2)3-4-11(9)13-7/h3-6H,1-2H3

Upstream product

• 15644-90-3 6-methoxy-2-methylquinolin-4-ol 
• 10025-87-3 trichlorophosphate 
• 58596-37-5 6-methoxy-2-methylquinolin-4(1H)-one 
• 104-94-9 4-methoxy-aniline 
• 33240-23-2 ethyl 3-((4-methoxyphenyl)amino)but-2-enoate 
• 80056-93-5 ethyl 3-[(4-methoxyphenyl)imino]butanoate 

Downstream Products

• 109980-03-2 N'-(6-methoxy-2-methyl-[4]quinolyl)-N,N-dimethyl-p-phenylenediamine 
• 94960-00-6 4-(6-methoxy-2-methyl-quinolin-4-ylamino)-benzenesulfonamide 
• 28102-96-7 2-methyl-4-mercapto-6-methoxyquinoline 
• 102441-71-4 bis-(6-methoxy-2-methyl-[4]quinolyl)-sulfide 
• 100462-38-2 (6-methoxy-2-methyl-[4]quinolyl)-phenyl-amine 
• 858451-70-4 N-(2-aminophenyl)-6-methoxy-2-methylquinolin-4-amine 
• 657367-83-4 N-(4-aminophenyl)-6-methoxy-2-methylquinolin-4-amine 

Relevant academic research and scientific papers

Synthesis of 6-methoxy-N 2,N 2,N 4,N 4,N 5,N 5-hexamethylquinoline-2,4,5-triamine - A new representative of quinoline proton sponges

[Figure not available: see fulltext.] We report the synthesis of 4-chloro-2-methyl-5-nitro- and 2,4-dichloro-5-nitroquinolines, containing methoxy groups at positions 6 and 8. The reaction of these compounds with dimethylamine solution in alcohol was shown to produce not only aminodehalogenation products, but also resulted in nucleophilic substitution of the methoxy groups. The reduction of 6-methoxy-N 2,N 2,N 4,N 4-tetramethyl-5-nitroquinoline-2,4-diamine with subsequent methylation gave 6-methoxy-N 2,N 2,N 4,N 4,N 5,N 5-hexamethylquinoline-2,4,5-triamine, a new representative of quinoline proton sponges.

Myobacterium Tuberculosis-Thioredoxin Reductase Inhibitor as an Antitubercular Agent

The invention relates to Mycobacterium tuberculosis-thioredoxin reductase inhibitors, processes for the preparation thereof, drugs containing said compounds, and the use of said compounds for manufacturing drugs.

ANTIMALARIAL COMPOUNDS

Antimalarial compounds of the formula: in which n is 1 or 2; X is C or N; R1 is a moiety comprising a secondary amine and a tertiary amine joined by a C2 to C4 alkyl chain; and R2 is CF3, F, or H, or an analog, combination, derivative, prodrug, stereoisomer, or pharmaceutically acceptable salt thereof. Pharmaceutical compounds including the antimalarial compounds. Methods of treating or preventing malaria comprising administering an effective amount of the antimalarial compounds.

Synthesis, Structure-Activity Relationship, and Antimalarial Efficacy of 6-Chloro-2-arylvinylquinolines

There is an urgent need to develop new efficacious antimalarials to address the emerging drug-resistant clinical cases. Our previous phenotypic screening identified styrylquinoline UCF501 as a promising antimalarial compound. To optimize UCF501, we herein report a detailed structure-activity relationship study of 2-arylvinylquinolines, leading to the discovery of potent, low nanomolar antiplasmodial compounds against a Plasmodium falciparum CQ-resistant Dd2 strain, with excellent selectivity profiles (resistance index 200). Several metabolically stable 2-arylvinylquinolines are identified as fast-acting agents that kill asexual blood-stage parasites at the trophozoite phase, and the most promising compound 24 also demonstrates transmission blocking potential. Additionally, the monophosphate salt of 24 exhibits excellent in vivo antimalarial efficacy in the murine model without noticeable toxicity. Thus, the 2-arylvinylquinolines represent a promising class of antimalarial drug leads.

Discovery of potent 4-aminoquinoline hydrazone inhibitors of NRH:quinoneoxidoreductase-2 (NQO2)

(NRH):quinone oxidoreductase 2 (NQO2) is associated with various processes involved in cancer initiation and progression probably via the production of ROS during quinone metabolism. Thus, there is a need to develop inhibitors of NQO2 that are active in v

Syntheses and evaluation of new Quinoline derivatives for inhibition of hnRNP K in regulating oncogene c-myc transcription

Aberrant overexpression of heterogeneous nuclear ribonucleoprotein K (hnRNP K) is a key feature in oncogenesis and progression of many human cancers. hnRNP K has been found to be a transcriptional activator to up-regulate c-myc gene transcription, a critical proto-oncogene for regulation of cell growth and differentiation. Therefore, down-regulation of c-myc transcription by inhibiting hnRNP K through disrupting its binding to c-myc gene promoter is a potential approach for cancer therapy. In the present study, we synthesized and screened a series of Quinoline derivatives and evaluated their binding affinity for hnRNP K. Among these derivatives, (E)-1-(4-methoxyphenyl)-3-(4-morpholino-6-nitroquinolin-2-yl)prop-2-en-1-one (compound 25) was determined to be the first-reported hnRNP K binding ligand with its KD values of 4.6 and 2.6 μM measured with SPR and MST, respectively. Subsequent evaluation showed that the binding of compound 25 to hnRNP K could disrupt its unfolding of c-myc promoter i-motif, resulting in down-regulation of c-myc transcription. Compound 25 showed a selective anti-proliferative effect on human cancer cell lines with IC50 values ranged from 1.36 to 3.59 μM. Compound 25 exhibited good tumor growth inhibition in a Hela xenograft tumor model, which might be related to its binding with hnRNP K. These findings illustrated that inhibition of DNA-binding protein hnRNP K by compound 25 could be a new and selective strategy of regulating oncogene transcription instead of targeting promoter DNA secondary structures such as G-quadruplexes or i-motifs.

Design, synthesis, and biological evaluation of AV6 derivatives as novel dual reactivators of latent HIV-1

The "shock and kill" strategy might be a promising therapeutic approach for HIV/AIDS due to the existence of latent viral reservoirs. A major challenge of the "shock and kill" strategy arises from the general lack of clinically effective latency-reversing

Green and Efficient Synthesis of 4-Heteryl-Quinolines and Their Antibacterial Evaluations

A green and efficient synthesis of 4-heteryl-quinolines (9a, 9b, 9c, 9d), (10a, 10b, 10c, 10d) and (11a, 11b, 11c, 11d) has been described using PEG-600 as a green solvent. Initially, 4-chloro-2-methylquinolines (5a, 5b, 5c, 5d) on reaction with aromatic heterocyclic thiols (6), (7), and (8) using PEG-600 at 100°C for 30–40 min resulted in (9), (10), and (11) in good yields. Alternatively, (9), (10), and (11) could also be prepared in dimethylformamide using K2CO3 as base and tetrabutylammonium bromide as phase transfer catalyst at 100°C for 1–2 h. All the compounds were synthesized and characterized by IR, NMR, mass spectroscopy, and 13C NMR analysis. All synthesized compounds were screened for their antibacterial activity against clinical strains that include Gram-positive (Bacillus subtilis MTCC 121, staphylococcus aureus MLS-16 MTCC 2940, Micrococcus lutes MTCC 2470, and Staphylococcus aureus MTCC 96) and Gram-negative bacteria (Candida albicans MTCC 3017, Klebsiella planticola MTCC 530, Escherichia coli MTCC 739, and Pseudomonas aeruginosa MTCC 2453). The results revealed that compounds (9a, 9d, 10a, 10c, 11b, and 11d) exhibited significant antibacterial activity almost equal to the standard drug, that is, Ciprofloxacin.

4-Nitro styrylquinoline is an antimalarial inhibiting multiple stages of Plasmodium falciparum asexual life cycle

Drugs against malaria are losing their effectiveness because of emerging drug resistance. This underscores the need for novel therapeutic options for malaria with mechanism of actions distinct from current antimalarials. To identify novel pharmacophores against malaria we have screened compounds containing structural features of natural products that are pharmacologically relevant. This screening has identified a 4-nitro styrylquinoline (SQ) compound with submicromolar antiplasmodial activity and excellent selectivity. SQ exhibits a cellular action distinct from current antimalarials, acting early on malaria parasite's intraerythrocytic life cycle including merozoite invasion. The compound is a fast-acting parasitocidal agent and also exhibits curative property in the rodent malaria model when administered orally. In this report, we describe the synthesis, preliminary structure-function analysis, and the parasite developmental stage specific action of the SQ scaffold.

Synthesis and antitubercular and antibacterial activity of some active fluorine containing quinoline–pyrazole hybrid derivatives

In an attempt to develop newer antitubercular and antibacterial agents against the increasing bacterial resistance, we have designed new quinoline–pyrazole analogs (8a–u) following the molecular hybridization approach. The structure of one of the final compounds, 8a was unambiguously confirmed by single crystal X-ray diffraction (SC-XRD) analysis. The target compounds were evaluated for their antitubercular activity against Mycobacterium tuberculosis and antibacterial activity against three common pathogenic bacterial strains. Four derivatives (8b, 8c, 8j and 8o) displayed significant antitubercular activity. The compounds derived from 8-trifluoromethylquinoline and 6-fluoroquinoline scaffolds with halogen substitution on the pyrazole ring exhibited superior inhibition activity than corresponding 6-methoxyquinoline analogs. The cytotoxic studies revealed that the active compounds are nontoxic to normal Vero cell lines with selectivity index values ≥10, which indicate the suitability of these compounds for further drug development. The in silico molecular docking study demonstrated strong binding affinity of the compounds with the target enzymes (InhA, CYP121 and TMPK) of M. tuberculosis. Further, the in vitro antibacterial activity of compounds 8b, 8c, 8d and 8g is comparable with that of the reference drug, Ciprofloxacin.