16778-21-5

Basic information

• Product Name: 4-Chloro-8-methoxyquinoline
• Synonyms: 4-CHLORO-8-METHOXYQUINOLINE;8-Methoxy-4-chloro quinoline;4-Chloro-8-Methoxyquinoline
• CAS NO: 16778-21-5
• Molecular Formula: C₁₀H₈ClNO
• Molecular Weight: 193.63
• EINECS: -0
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 16778-21-5.mol

Chemical Properties

• Melting Point: 79-80 °C
• Boiling Point: 299.9 °C at 760 mmHg
• Flash Point: 135.2 °C
• Appearance: /
• Density: 1.267 g/cm³
• Vapor Pressure: 0.00207mmHg at 25°C
• Refractive Index: 1.621
• Storage Temp.: -20?C Freezer
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 1.86±0.30(Predicted)
• CAS DataBase Reference: 4-Chloro-8-methoxyquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-8-methoxyquinoline(16778-21-5)
• EPA Substance Registry System: 4-Chloro-8-methoxyquinoline(16778-21-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 16778-21-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-8-methoxyquinoline is used as a potent selective CRTh2 (DP2) antagonist for the potential treatment of asthma, allergic rhinitis, and other inflammatory diseases. Its antagonistic properties make it a valuable compound in the development of medications targeting these conditions.
Used in Chemical Research:
As a quinoline derivative, 4-Chloro-8-methoxyquinoline may also be utilized in chemical research and development for the synthesis of other compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

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

Upstream product

• 21269-34-1 4-hydroxy-8-methoxyquinoline 
• 28027-18-1 4-hydroxy-8-methoxyquinoline-3-carboxylic acid 
• 27568-04-3 Ethyl 4-hydroxy-8-methoxyquinoline-3-carboxylate 
• 25165-68-8 5-[(2-methoxy-phenylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 104007-09-2 2-[(2-methoxyphenylamino)-methylene]-malonic acid diethyl ester 
• 90-04-0 2-methoxy-phenylamine 

Downstream Products

• 7621-73-0 N⁴,N⁴-diethyl-N¹-(8-methoxy-[4]quinolyl)-1-methyl-butanediyldiamine 
• 57334-36-8 4-chloro-8-hydroxyquinoline 
• 131666-46-1 (8-Methoxy-quinolin-4-yl)-o-tolyl-amine 
• 63352-82-9 8-Methoxy-4-phenylquinoline 
• 145297-36-5 8-Methoxy-7-nitro-4-phenylquinoline 
• 145297-34-3 4-(4-Bromophenyl)-8-methoxy-5-nitroquinoline 
• 145297-33-2 4-(3,4-Dimethoxyphenyl)-8-methoxy-5-nitroquinoline 
• 145013-67-8 8-Methoxy-5-nitro-4-phenylquinoline 
• 145013-69-0 8-Methoxy-4-(4-methoxyphenyl)-5-nitroquinoline 
• 145013-70-3 5-amino-8-methoxy-4-phenylquinoline 
• 145013-73-6 6-bromo-8-methoxy-4-phenylquinoline-5-amine 
• 145013-72-5 8-Methoxy-4-(4-methoxy-phenyl)-quinolin-5-ylamine 
• 145013-75-8 5-Azido-8-methoxy-4-phenyl-quinoline 
• 145013-78-1 5-Azido-6-bromo-8-methoxy-4-phenyl-quinoline 

Relevant articles and documents

INHIBITORS FOR THE TREATMENT OF CANCER AND RELATED METHODS

Some embodiments of the invention include inventive compounds. Other embodiments include compositions (e.g., pharmaceutical compositions) comprising the inventive compound. Still other embodiments of the invention include compositions (e.g., pharmaceutica

Synthesis and anti-tumor activities of 4-anilinoquinoline derivatives

Twenty-two 7-fluoro (or 8-methoxy)-4-anilinoquinolines compounds were designed and synthesized as potentially potent and selective antitumor inhibitors. All the prepared compounds were evaluated for their in vitro antiproliferative activities against the HeLa and BGC823 cell lines. Ten compounds (1a-g; 2c; 2e and 2i) exhibited excellent antitumor activity superior to that of gefitinib. Among the ten compounds; seven (1a-c; 1e-1g and 2i) displayed excellent selectivity for BGC823 cells. In particular; 1f and 2i exhibited potent cytotoxic activities against HeLa cells and BGC823 cells with better IC50 values than gefitinib.

SELECTIVE PFKFB4 INHIBITORS FOR THE TREATMENT OF CANCER

Methods and pharmaceutical compositions for inhibiting 6-phosphofructo-2-kinase/fructose-2,6-biphosphatase 4 (PFKFB4) and the treatment of cancer are described.

Discovery of 4-(4-(2-((5-Hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)(propyl) amino)ethyl)piperazin-1-yl)quinolin-8-ol and its analogues as highly potent dopamine D2/D3 agonists and as iron chelator: In vivo activity indicates potential application in symptomatic and neuroprotective therapy for Parkinson's disease

The role of iron in the pathogenesis of Parkinson's disease (PD) has been implicated strongly because of generation of oxidative stress leading to dopamine cell death. In our overall goal to develop bifunctional/multifunctional drugs, we designed dopamine D2/D3 agonist molecules with a capacity to bind to iron. Binding assays were carried out with HEK-293 cells expressing either D2 or D3 receptor with tritiated spiperone to evaluate inhibition constants (K i). Functional activity of selected compounds was carried out with GTPyS binding assay. SAR results identified compounds (+)-19a and (-)-19b as two potent agonists for both D2 and D3 receptors (EC50 (GTPyS); D2 = 4.51 and 1.69 nM and D3 = 1.58 and 0.74 nM for (-)-19b and (+)-19a, respectively). In vitro complexation studies with 19b demonstrated efficient chelation with iron. Furthermore, the deoxyribose assay with 19b demonstrated potent antioxidant activity. In PD animal model study, (-)-19b exhibited potent in vivo activity in reversing locomotor activity in reserpinized rats and also in producing potent rotational activity in 6-OHDA lesioned rats. This reports initial development of unique lead molecules that might find potential use in symptomatic and neuroprotective treatment of PD.

Improved Syntheses of Some Monohloro- and Monobromo-8-quinolinols

Procedures were developed for the preparation of the 2-, 3-, 4-, and 6-monosubstituted chloro and bromo 8-quinolinols which afforded greater yields and/or reduced the number of steps in the preparation. 100 MHz 1H-NMR spetra for the 12 possible monochloro