53342-53-3

Basic information

• Product Name: 4,6-DICHLORO-2-METHYLQUINOLINE
• Synonyms: 4,6-DICHLORO-2-METHYLQUINOLINE;4,6-DICHLOROQUINALDINE
• CAS NO: 53342-53-3
• Molecular Formula: C₁₀H₇Cl₂N
• Molecular Weight: 212.08
• Mol File: 53342-53-3.mol
• Article Data: 13

Chemical Properties

• Melting Point: 83.0 to 87.0 °C
• Boiling Point: 291.4 °C at 760 mmHg
• Flash Point: 157.7 °C
• Appearance: /
• Density: 1.351 g/cm³
• Vapor Pressure: 0.00341mmHg at 25°C
• Refractive Index: 1.643
• Solubility: soluble in Chloroform
• CAS DataBase Reference: 4,6-DICHLORO-2-METHYLQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-DICHLORO-2-METHYLQUINOLINE(53342-53-3)
• EPA Substance Registry System: 4,6-DICHLORO-2-METHYLQUINOLINE(53342-53-3)

Safety Data

• Hazard Codes: T
• Statements: 25-41
• Safety Statements: 26-39-45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 53342-53-3(Hazardous Substances Data)

Usage

General Description

4,6-Dichloro-2-methylquinoline is a synthetic chemical compound belonging to the class of organic compounds called quinolines; specifically, it is a member of the methylquinolines sub-category. As its name suggests, this specific compound has chlorine atoms at the 4th and 6th positions of the quinoline ring and a methyl group at the 2nd position. Given its specialized structure, it finds utility in various applications such as pharmaceuticals, dyes, and research. Given its active functional groups and chloro-derivatives, it could potentially exhibit anti-microbial properties, although more research would be required to determine this with certainty. Like all chemicals, it should be handled with proper safety measures to ensure that no adverse health effects take place from any exposure or misuse.

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

Upstream product

• 15644-86-7 6-chloro-2-methyl-quinolin-4-ol 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 108063-18-9 N'-(6-chloro-2-methyl-[4]quinolyl)-N,N-dimethyl-p-phenylenediamine 
• 109650-36-4 4-(6-chloro-2-methyl-[4]quinolylamino)-benzoic acid ; hydrochloride 
• 66735-24-8 4-Amino-6-chlor-2-methylchinolin 
• 4133-05-5 2-chloro-6,9-dimethyldibenzo[b,h][1,6]naphthyridine 

Relevant articles and documents

Discovery of fast-acting dual-stage antimalarial agents by profiling pyridylvinylquinoline chemical space via copper catalyzed azide-alkyne cycloadditions

To identity fast-acting, multistage antimalarial agents, a series of pyridylvinylquinoline-triazole analogues have been synthesized via CuAAC. Most of the compounds display significant inhibitory effect on the drug-resistant malarial Dd2 strain at low submicromolar concentrations. Among the tested analogues, compound 60 is the most potent molecule with an EC50 value of 0.04 ± 0.01 μM. Our current study indicates that compound 60 is a fast-acting antimalarial compound and it demonstrates stage specific action at the trophozoite phase in the P. falciparum asexual life cycle. In addition, compound 60 is active against both early and late stage P. falciparum gametocytes. From a mechanistic perspective, compound 60 shows good activity as an inhibitor of β-hematin formation. Collectively, our findings suggest that fast-acting agent 60 targets dual life stages of the malarial parasites and warrant further investigation of pyridylvinylquinoline hybrids as new antimalarials.

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.

Design, synthesis and cytotoxicity of novel 2-arylvinyl-4- aminoquinoline derivatives

With an aim to develop promising anti-tumor agents, a novel series of 2-arylvinyl-4-aminoquinoline derivatives were designed, synthesized and evaluated for their cytotoxicity against H-460, HT-29, HepG2 and SGC-7901 cell lines in vitro. The pharmacological results indicated that most compounds were more potent than the positive controls, especially compounds 8, 14 and 16 with IC50 values ranging from 0.05 to 0.85 μM against all tested cell lines respectively, which were 5.7- to 112-fold better than Iressa. The most active compound 14 (IC50 values of 0.05, 0.25, 0.16, 0.68 μM), bearing 4-fluorostyryl at C-2 position and 3-(dimethylamino)-1-propylamino at C-4 position, showed great promise as a lead for the development of more effective quinoline analogues.