68500-37-8

Basic information

• Product Name: 4-Chloro-7-methoxyquinoline
• Synonyms: 4-CHLORO-7-METHOXYQUINOLINE;7-Methoxy-4-chloroquinoline;Quinoline, 4-chloro-7-methoxy-;4-Cholro-7-Methoxyquinoline;4-Chloro-7-methoxy-1-azanaphthalene;4-Chloro-7-methoxyquinoline, >=97%
• CAS NO: 68500-37-8
• Molecular Formula: C₁₀H₈ClNO
• Molecular Weight: 193.63
• EINECS: -0
• Mol File: 68500-37-8.mol
• Article Data: 13

Chemical Properties

• Melting Point: 75-77
• Boiling Point: 299.881 °C at 760 mmHg
• Flash Point: 135.163 °C
• Appearance: /
• Density: 1.268 g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.622
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 3.89±0.27(Predicted)
• CAS DataBase Reference: 4-Chloro-7-methoxyquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-7-methoxyquinoline(68500-37-8)
• EPA Substance Registry System: 4-Chloro-7-methoxyquinoline(68500-37-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 68500-37-8(Hazardous Substances Data)

Usage

Chemical Properties

yellow powder

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

Upstream product

• 190516-85-9 7-methoxy-4(1H)-oxoquinoline 
• 82121-05-9 4-hydroxy-7-methoxyquinoline 

Downstream Products

• 6238-12-6 7-methoxy-4-methyl-quinoline 
• 948571-12-8 N-(1,3-dimethyl-1H-pyrazol-4-yl)-2-[2-methoxy-4-(7-methoxyquinolin-4-yloxy)phenyl]acetamide 
• 1361235-65-5 7-methoxy-4-(3-methoxy-4-nitrophenoxy)quinoline 
• 1361235-70-2 N-(5-(7-methoxyquinolin-4-yloxy)pyrimidin-2-yl)benzamide 
• 1361235-67-7 N-(2-methoxy-4-(7-methoxyquinolin-4-yloxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide 
• 1361235-66-6 2-methoxy-4-(7-methoxyquinolin-4-yloxy)aniline 

Relevant articles and documents

Design and synthesis of 4(1H)-quinolone derivatives as autophagy inducing agents by targeting ATG5 protein

Background: Quinolines have been characterized as a class of potential antitumor agents, and a large number of natural and synthetic quinolines acting as antitumor agents were reported. Methods: A series of 7-chloro-4(1H)-quinolone derivatives were synthesized. The antiproliferative effect of these compounds was evaluated by MTT assay against five human tumor cell lines. The mechanism of action of the selected compound 7h was also investigated. Results and Discussion: Most of the compounds had more potent antiproliferative activities than the lead compound 7-chloro-4(1H)-quinolone 6b. Compound 7h was found to be the most potent antiproliferative agent against human tumor cell lines. Further investigation demonstrated that compound 7h triggered ATG5-dependent autophagy of colorectal cancer cells by promoting the functions of LC3 proteins. Conclusion: These results were useful for designing and discovering more potent novel antitumor agents endowed with better pharmacological profiles.

Design, synthesis and biological evaluation of new quinoline derivatives as potential antitumor agents

A series of new quinoline derivatives was designed, synthesized and evaluated for their antiproliferative activity. The results demonstrated that compounds 11p, 11s, 11v, 11x and 11y exhibited potent antiproliferative activity with IC50 value of lower than 10 μM against seven human tumor cell lines, and N-(3-methoxyphenyl)-7- (3-phenylpropoxy)quinolin-4-amine 11x was found to be the most potent antiproliferative agent against HCT-116, RKO, A2780 and Hela cell lines with an IC50 value of 2.56, 3.67, 3.46 and 2.71 μM, respectively. The antitumor efficacy of the representative compound 11x in mice was also evaluated, and the results showed that compound 11x effectively inhibited tumor growth and decreased tumor weight in animal models. Further investigation on mechanism of action indicated that compound 11x could inhibit colorectal cancer growth through ATG5-depenent autophagy pathway. Therefore, these quinoline derivatives are a new class of molecules that have the potential to be developed as new antitumor drugs.

Preparation method and applications of triazolo-thiadiazole c-Met kinase inhibitor

The invention relates to the field of pharmaceutical chemistry, and specifically relates to [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives, a preparation method thereof, a pharmaceutical composition comprising the same, and medical applications thereof, in particular, an application as a c-Met kinase inhibitor.