190728-24-6

Basic information

• Product Name: Quinoline, 6,7-dimethoxy-4-(4-nitrophenoxy)-
• Synonyms: Quinoline, 6,7-dimethoxy-4-(4-nitrophenoxy)-;6,7-dimethoxy-4-(4-nitrophenoxy)-Quinoline
• CAS NO: 190728-24-6
• Molecular Formula: C₁₇H₁₄N₂O₅
• Molecular Weight: 326.30346
• Mol File: 190728-24-6.mol

Chemical Properties

• Boiling Point: 480.9±40.0 °C(Predicted)
• Appearance: /
• Density: 1.319±0.06 g/cm3(Predicted)
• PKA: 4.33±0.30(Predicted)
• CAS DataBase Reference: Quinoline, 6,7-dimethoxy-4-(4-nitrophenoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: Quinoline, 6,7-dimethoxy-4-(4-nitrophenoxy)-(190728-24-6)
• EPA Substance Registry System: Quinoline, 6,7-dimethoxy-4-(4-nitrophenoxy)-(190728-24-6)

Safety Data

• Hazardous Substances Data: 190728-24-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Quinoline, 6,7-dimethoxy-4-(4-nitrophenoxy)is utilized as a building block in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs that can target specific biological pathways, making it a valuable component in medicinal chemistry.
Used in Agrochemical Industry:
Quinoline, 6,7-dimethoxy-4-(4-nitrophenoxy)also serves as a key intermediate in the production of agrochemicals. Its incorporation into agrochemical formulations can contribute to the development of effective pest control and crop protection products.
Used in Drug Development:
Due to its potential biological activities, including anti-inflammatory and anti-tumor properties, Quinoline, 6,7-dimethoxy-4-(4-nitrophenoxy)is studied for its application in drug development. Researchers are interested in exploring its therapeutic potential for treating various diseases and conditions.
Used in Bioactive Molecule Synthesis:
The presence of the nitro group and methoxy groups in the structure of Quinoline, 6,7-dimethoxy-4-(4-nitrophenoxy)makes it a versatile compound for the synthesis of new bioactive molecules. These molecules can be further explored for their potential applications in various fields, such as medicine, agriculture, and materials science.

Upstream product

• 100-02-7 4-nitro-phenol 
• 35654-56-9 6,7-dimethoxy-4-chloroquinoline 
• 144-55-8 sodium hydrogencarbonate 
• 13425-93-9 6,7-dimethoxyquinoline-4-ol 
• 350-46-9 4-Fluoronitrobenzene 
• 4101-32-0 4',5'-dimethoxy-2'-nitroacetophenone 
• 213699-53-7 5-(((3,4-dimethoxyphenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 26893-22-1 1,4-Dihydro-6,7-dimethoxy-4-oxo-3-quinolinecarboxylic acid 
• 6315-89-5 3,4-dimethoxyaniline 
• 13436-14-1 ethyl 6,7-dimethoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylate 
• 127285-54-5 1,4-dihydro-6,7-dimethoxy-4-oxoquinoline 
• 4101-30-8 2-amino-4,5-dimethoxyacetophenone 
• 498-02-2 1-(3-methoxy-4-hydroxyphenyl)ethanone 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 

Downstream Products

• 190728-25-7 4-((6,7-dimethoxyquinolin-4-yl)oxy)aniline 
• 1192299-05-0 N-[4-(6,7-dimethoxyquinolin-4-yloxy)phenyl]-2-trifluoromethylbenzenesulfonamide 
• 1140909-48-3 Cabozantinib malate salt 
• 849217-68-1 cabozantinib 
• 190727-05-0 N-{4-[(6,7-Dimethoxy-4-quinolinyl)oxy]phenyl}-(4-nitrophenyl)carboxamide 
• 190726-66-0 Ki₆₉₄₅ 

Relevant articles and documents

One-step synthesis of [18F]cabozantinib for use in positron emission tomography imaging of c-Met

Cabozantinib is an FDA-approved kinase inhibitor for the treatment of medullary thyroid cancer and advanced renal cell carcinoma, which exerts its therapeutic effect by inhibiting, among others, the tyrosine kinase c-Met. Noninvasive imaging techniques are becoming increasingly important clinically to ensure drug efficacy, staging, monitoring, and patient stratification. PET isotope labelled tyrosine kinase inhibitors have, for the same reason, potential as PET tracers for imaging of various cancers. On the basis of cabozantinib, we synthesized the novel boronic acid pinacol ester 4 as a labelling precursor, where the boronic ester moiety replaces the fluorine native to this kinase inhibitor. By this, we wanted to explore whether recently developed Cu-mediated fluorination methods are adaptable to more complex substrates and thereby provide easy access to [18F]cabozantinib directly. Hydrolysis was implemented before preparative purification due to challenges with on-column hydrolysis of the precursor 4, and [18F]cabozantinib was obtained in ≥99% radiochemical purity and in 2.8?±?0.05% (n?=?4) isolated decay corrected yield in a synthesis time of 90?minutes. The molar activity of representative batches was determined to be 17?±?8?GBq/μmol.

Design, synthesis and biological evaluation of 6-substituted quinolines derived from cabozantinib as c-Met inhibitors

Based on the cabozantinib scaffold, novel c-Met inhibitors were rationalized from the limited knowledge of structure-activity relationships for the quinoline 6-position. Emphasis was given to modifications capable of engaging in additional polar interacti

Synthesis and antiproliferative evaluation of novel N-arylquinolones

Abstract: Novel N-aryl-substituted quinolones were evaluated for antiproliferative activity. The chemical modifications were inspired by previously reported cytotoxic agents with structural similarities. Dimethylated anilines displayed the most potent effect in the renal cancer cell line Caki-1 and the breast cancer cell line MDA-MB-231, with GI50 values down to 24 μM. Further evaluation in the NCI60 cell lines revealed growth inhibition up to 50%, with the strongest effect observed in renal and lung cancer cell lines. In silico ADMET evaluation indicated favorable characteristics for both gastrointestinal and CNS uptake. The potential toxic electrophilic α,β-unsaturated carbonyl functionalities were shown to be inert to ethanethiol. Graphic abstract: [Figure not available: see fulltext.]

COMPOUNDS FOR THE TREATMENT OF KINASE-DEPENDENT DISORDERS

The present invention relates to compounds that modulate cellular activities such as proliferation, differentiation, programmed cell death, migration, and chemoinvasion, by modulating protein kinase enzymatic activity, and compositions thereof, and methods of using such compounds.

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.

Method of Treating Cancer and Bone Cancer Pain

This invention is directed to the treatment of cancer, particularly lung cancer, breast cancer, melanoma, renal cell carcinoma, thyroid cancer that has metastasized to the bone. The invention is also directed to a method for treating bone cancer pain in a

Method of Treating Cancer

This invention is directed to the treatment of cancer, particularly castration-resistant prostate cancer and osteoblastic bone metastases, with a dual inhibitor of MET and VEGF.

Design, synthesis, and biological evaluation of 4-((6,7-dimethoxyquinoline-4-yl)oxy)aniline derivatives as FLT3 inhibitors for the treatment of acute myeloid leukemia

FMS-like tyrosine kinase 3 (FLT3) was an important therapeutic target in acute myeloid leukemia (AML). We synthesized two series of 4-((6,7-dimethoxyquinoline-4-yl)oxy)aniline derivatives possessing the semicarbazide moiety and 2,2,2-trifluoro-N,N′-dimeth

Optimization and biological evaluation of nicotinamide derivatives as Aurora kinase inhibitors

Aurora kinases are known to be overexpressed in various solid tumors and implicated in oncogenesis and tumor progression. A series of nicotinamide derivatives were synthesized and their biological activities were evaluated, including kinase inhibitory act

Design, synthesis and evaluation of sulfonylurea-containing 4-phenoxyquinolines as highly selective c-Met kinase inhibitors

Deregulation of receptor tyrosine kinase c-Met has been reported in human cancers and is considered as an attractive target for small molecule drug discovery. In this study, a series of 4-phenoxyquinoline derivatives bearing sulfonylurea moiety were designed, synthesized and evaluated for their c-Met kinase inhibition and cytotoxicity against tested four cell lines in vitro. The pharmacological data indicated that most of the tested compounds showed moderate to significant potency as compared with foretinib, with the most promising compound 13x (c-Met kinase IC50 = 1.98 nM) demonstrated relatively good selectivity versus 10 other tyrosine kinases and remarkable cytotoxicities against HT460, MKN-45, HT-29 and MDA-MB-231 with IC50 values of 0.055 μM, 0.064 μM, 0.16 μM and 0.49 μM, respectively. The preliminary structure activity relationships indicated that a sulfonylurea moiety as linker as well as mono-EGWs (such as R1 = 4-F) on the terminal phenyl rings contributed to the antitumor activity.