35654-56-9

Basic information

• Product Name: 4-CHLORO-6,7-DIMETHOXYQUINOLINE
• Synonyms: 6,7-DIMETHOXY-4-CHLOROQUINOLINE;4-CHLORO-6,7-DIMETHOXYQUINOLINE;4-Chloro-6,7-dimethoxyquioline;Quinoline, 4-chloro-6,7-dimethoxy-;4-CHLORO-6,7-DIMETHOXYQUINOLINE(35654-56-9)
• CAS NO: 35654-56-9
• Molecular Formula: C₁₁H₁₀ClNO₂
• Molecular Weight: 223.66
• EINECS: -0
• Product Categories: Quinoline&Isoquinoline
• Mol File: 35654-56-9.mol
• Article Data: 54

Chemical Properties

• Melting Point: 132.0 to 136.0 °C
• Boiling Point: 325.197 °C at 760 mmHg
• Flash Point: 150.474 °C
• Appearance: /
• Density: 1.265 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.95±0.30(Predicted)
• CAS DataBase Reference: 4-CHLORO-6,7-DIMETHOXYQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-6,7-DIMETHOXYQUINOLINE(35654-56-9)
• EPA Substance Registry System: 4-CHLORO-6,7-DIMETHOXYQUINOLINE(35654-56-9)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45-24/25
• RIDADR: UN2811
• HazardClass: IRRITANT
• Hazardous Substances Data: 35654-56-9(Hazardous Substances Data)

Usage

Description

4-Chloro-6,7-dimethoxyquinoline is a light brown powder that serves as an intermediate in the synthesis of various pharmaceutical and biologically active compounds. It is a key component in the preparation of Tivozanib (T447205) and Cabozantinib (C051500), which are both utilized as anticancer agents.

Uses

Used in Pharmaceutical Industry:
4-Chloro-6,7-dimethoxyquinoline is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its primary application is in the preparation of Tivozanib (T447205) and Cabozantinib (C051500), which are employed as anticancer agents. These compounds exhibit significant potential in the treatment of cancer due to their ability to inhibit specific cellular pathways and target cancer cells effectively.
Used in Anticancer Applications:
4-Chloro-6,7-dimethoxyquinoline plays a crucial role in the development of Tivozanib and Cabozantinib, which are used as anticancer agents. These agents target specific cellular pathways involved in cancer cell growth and proliferation, thereby inhibiting tumor progression and offering potential therapeutic benefits to patients suffering from various types of cancer.

InChI:InChI=1/C11H10ClNO2/c1-14-10-5-7-8(12)3-4-13-9(7)6-11(10)15-2/h3-6H,1-2H3

Upstream product

• 13425-93-9 6,7-dimethoxyquinoline-4-ol 
• 127285-54-5 1,4-dihydro-6,7-dimethoxy-4-oxoquinoline 
• 26717-39-5 [[(3,4-Dimethoxyphenyl)amino]methylene]malonic acid,diethyl ester 
• 13436-14-1 ethyl 6,7-dimethoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylate 
• 6315-89-5 3,4-dimethoxyaniline 
• 26893-22-1 1,4-Dihydro-6,7-dimethoxy-4-oxo-3-quinolinecarboxylic acid 
• 4101-30-8 2-amino-4,5-dimethoxyacetophenone 
• 213699-53-7 5-(((3,4-dimethoxyphenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 26893-22-1 4-hydroxy-6,7-dimethoxy-2-quinolinecarboxylic acid 
• 13436-14-1 ethyl 4-hydroxy-6,7-dimethoxyquinoline-3-carboxylate 
• 67000-01-5 methyltertbutyl ether 
• 1634-04-4 tert-butyl methyl ether 
• 96042-30-7 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 

Downstream Products

• 190726-45-5 Ki₆₇₈₃ 
• 202917-05-3 6,7-Dimethoxy-4-(3-nitro-phenoxy)-quinoline 
• 319492-82-5 CA₇₅ 
• 190728-24-6 6,7?dimethoxy?4?(4?nitrophenoxy)quinoline 

Relevant articles and documents

Design, Synthesis and Biological Evaluation of Novel α-Acyloxycarboxamide-Based Derivatives as c-Met Inhibitors

Dysregulated HGF/c-Met signalling has been associated with many human cancers, poor clinical outcomes, and even resistance acquisition to some approved targeted therapies. As such, c-Met kinase has emerged as an attractive target for anticancer drug discovery. Herein, a series of 6,7-disubstitued-4-(2-fluorophenoxy)quinoline derivatives bearing α-acyloxycarboxamide moiety were designed, synthesized via Passerini reaction as the key step, and evaluated for their in vitro biological activities against c-Met kinase and five selected cancer cell lines. The preliminary structure-activity relationship demonstrated that α-acyloxycarboxamide as the 5-atom linker maintained the potent antitumor potency. Among these compounds, compound 25s (c-Met IC50 = 4.06 nmol/L) was identified as the most promising lead compound and displayed the most potent antiproliferative activities against A549, HT-29 and MDA-MB-231 cell lines with IC50 of 0.39, 0.20, and 0.58 μmol/L, which were 1.3-, 1.4- and 1.2-fold superior to foretinib, respectively. The further studies indicated that compound 25s can induce apoptosis of A549 cells and arrest efficiently the cell cycle distribution in G2/M phase of A549 cells. Moreover, compound 25s can also inhibit c-Met phosphorylation in A549 cells by a dose-dependent manner. Collectively, these results indicated that compound 25s could be a potential anticancer lead compound deserving for further development.

Structure-based discovery of novel 4-(2-fluorophenoxy)quinoline derivatives as c-Met inhibitors using isocyanide-involved multicomponent reactions

The c-Met kinase has emerged as a promising target for the development of small molecule antitumor agents because of its close relationship with the progression of many human cancers, poor clinical outcomes and even drug resistance. In this study, two novel series of 6,7-disubstitued-4-(2-fluorophenoxy)quinoline derivatives containing α-acyloxycarboxamide or α-acylaminoamide scaffolds were designed, synthesized, and evaluated for their in vitro biological activities against c-Met kinase and four cancer cell lines (H460, HT-29, MKN-45, and MDA-MB-231). Most of the target compounds exhibited moderate to significant potency and possessed selectivity for H460 and HT-29 cancer cell lines. The preliminary structure-activity relationships indicated that α-acyloxycarboxamide or α-acylaminoamide as 5-atom linker contributed to the antitumor potency. Among these compounds, compound 10m (c-Met IC50 = 2.43 nM, a multitarget tyrosine kinase inhibitor) exhibited the most potent inhibitory activities against H460, HT-29 and MDA-MB-231 cell lines with IC50 of 0.14 ± 0.03 μM, 0.20 ± 0.02 μM and 0.42 ± 0.03 μM, which were 1.7-, 1.3- and 1.6-fold more active than foretinib, respectively. In addition, concentration-dependent assay and time-dependent assay indicated compound 10m can inhibit the proliferation of H460 cell in a time and concentration dependent manner. Moreover, docking studies revealed the common mode of interaction with the c-Met binding site, suggesting that 10m is a potential candidate for cancer therapy deserving further study.

Novel substituted pyrazolo [1, 5-a] pyrimidine compound and preparation method and application thereof

The invention provides a novel substituted pyrazolo [1, 5-a]pyrimidine compound and a preparation method and application thereof, and particularly relates to a pyrazolo [1, 5-a]pyrimidine-containing quinoline derivative shown as a general formula (I) and pharmaceutically acceptable salts thereof, and substituent groups X, Ar and A have meanings given in the specification. The invention also relates to a compound represented by the general formula (I), wherein the compound has a strong c-Met kinase inhibition effect. The invention also relates to application of the compound and the pharmaceutically acceptable salt thereof in preparation of drugs for treating and/or preventing diseases caused by abnormal high expression of c-Met kinase, especially application in preparation of drugs for treating and/or preventing cancers.