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4-[(6,7-DiMethoxy-4-quinolyl)oxy]-2-chloroaniline, also known as para-quinonlinyl chloroaniline, is a heterocyclic chemical compound with the molecular formula C16H14ClNO3. It features a quinoline ring system, a chlorine atom, and an aniline group, making it a versatile molecule with potential applications in various industries.

286371-44-6

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286371-44-6 Usage

Uses

Used in Dye and Pigment Production:
4-[(6,7-DiMethoxy-4-quinolyl)oxy]-2-chloroaniline is used as a key intermediate in the production of dyes and pigments for various applications, such as textiles, plastics, and printing inks. Its unique chemical structure contributes to the color properties and stability of the resulting dyes and pigments.
Used in Pharmaceutical Manufacturing:
In the pharmaceutical industry, 4-[(6,7-DiMethoxy-4-quinolyl)oxy]-2-chloroaniline is used as a building block for the synthesis of various drugs. Its heterocyclic structure allows for the development of new medicinal compounds with potential therapeutic effects.
Used in Agrochemical Production:
4-[(6,7-DiMethoxy-4-quinolyl)oxy]-2-chloroaniline is also utilized in the agrochemical sector for the development of pesticides and other crop protection agents. Its chemical properties can be harnessed to create effective and targeted agrochemicals.
Used in Antitumor Applications:
As a potential antitumor agent, 4-[(6,7-DiMethoxy-4-quinolyl)oxy]-2-chloroaniline is used in research for its ability to inhibit the growth of cancer cells. Its unique structure may offer new avenues for the development of cancer treatments, although further studies are needed to fully understand its mechanism of action and potential side effects.
It is crucial to handle 4-[(6,7-DiMethoxy-4-quinolyl)oxy]-2-chloroaniline with care due to its potential toxic or harmful effects if not properly managed. Proper safety measures and guidelines should be followed during its production, use, and disposal to minimize any risks associated with 4-[(6,7-DiMethoxy-4-quinolyl)oxy]-2-chloroaniline.

Check Digit Verification of cas no

The CAS Registry Mumber 286371-44-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,8,6,3,7 and 1 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 286371-44:
(8*2)+(7*8)+(6*6)+(5*3)+(4*7)+(3*1)+(2*4)+(1*4)=166
166 % 10 = 6
So 286371-44-6 is a valid CAS Registry Number.

286371-44-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-chloroaniline

1.2 Other means of identification

Product number -
Other names 2-chloro-4-((6,7-dimethoxyquinolin-4-yl)oxy)aniline

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:286371-44-6 SDS

286371-44-6Relevant articles and documents

Preparation method of VEGFR inhibitor tevozanib

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Paragraph 0037; 0047-0055, (2022/03/27)

The invention relates to a preparation method of a VEGFR (vascular endothelial growth factor receptor) inhibitor tevozanib. Compared with the prior art, according to the preparation method, the compound shown in the formula 1 and the compound shown in the formula 2 are selected to react, the reaction reagent compound shown in the formula 3 is prepared firstly, then the reaction reagent compound shown in the formula 3 and the hydroxyl of the compound shown in the formula 4 are subjected to the substitution reaction, the reaction site of the reaction is single, the yield is excellent, and reaction purification is convenient; the method provided by the invention has the advantages of simple operation process, low purification cost and high overall yield, and is suitable for industrial large-scale production of bulk pharmaceutical chemicals, and the process steps for synthesizing and preparing the tevozanib are simplified.

NOVEL COMPOUNDS AND COMPOSITION FOR TARGETED THERAPY OF KIDNEY-ASSOCIATED CANCERS

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Paragraph 000329-000330, (2021/07/31)

The present invention provides therapeutic compounds of the following formula I: or pharmaceutically acceptable salts, hydrates, or solvates thereof that are therapeutic or anticancer agents, pharmaceutical compositions containing them, methods for their

Discovery of 2-(4-Chloro-3-(trifluoromethyl)phenyl)- N-(4-((6,7-dimethoxyquinolin-4-yl)oxy)phenyl)acetamide (CHMFL-KIT-64) as a Novel Orally Available Potent Inhibitor against Broad-Spectrum Mutants of c-KIT Kinase for Gastrointestinal Stromal Tumors

Liu, Qingsong,Wu, Yun,Wang, Beilei,Wang, Junjie,Qi, Shuang,Zou, Fengming,Qi, Ziping,Liu, Feiyang,Liu, Qingwang,Chen, Cheng,Hu, Chen,Hu, Zhenquan,Wang, Aoli,Wang, Li,Wang, Wenchao,Ren, Tao,Cai, Yujiao,Bai, Mingfeng,Liu, Jing

, p. 6083 - 6101 (2019/08/02)

Starting from our previously developed c-KIT kinase inhibitor CHMFL-KIT-8140, through a type II kinase inhibitor binding element hybrid design approach, we discovered a novel c-KIT kinase inhibitor compound 18 (CHMFL-KIT-64), which is potent against c-KIT wt and a broad spectrum of drug-resistant mutants with improved bioavailability. 18 exhibits single-digit nM potency against c-KIT kinase and c-KIT T670I mutants in the biochemical assay and displays great potencies against most of the gain-of-function mutations in the juxtamembrane domain, drug-resistant mutations in the ATP binding pocket (except V654A), and activation loops (except D816V). In addition, 18 exhibits a good in vivo pharmacokinetic (PK) profile in different species including mice, rats, and dogs. It also displays good in vivo antitumor efficacy in the c-KIT T670I, D820G, and Y823D mutant-mediated mice models as well as in the c-KIT wt patient primary cells which are known to be imatinib-resistant. The potent activity against a broad spectrum of clinically important c-KIT mutants combining the good in vivo PK/pharmacodynamic properties of 18 indicates that it might be a new potential therapeutic candidate for gastrointestinal stromal tumors.

Tyrosine kinase inhibitor and application thereof

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Paragraph 0013; 0036; 0038; 0039, (2018/09/08)

The invention discloses a tyrosine kinase inhibitor. A chemical name of the tyrosine kinase inhibitor is 1-(2-chloro-4-((6,7-dimethoxyquinoline-4-yl)oxy)phenyl)-3-(4-fluorophenyl)carbamide and a structure is shown as a formula (I). Meanwhile, the inventio

Preparation method for Tivozanib

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Paragraph 0024, (2017/08/29)

The invention belongs to the technical field of the biological medicine, and particularly relates to a preparation method for Tivozanib. The preparation method comprises the following steps: firstly using N-[2-chlorine-4-hydroxy-phenyl]-N'-(5-methyl-3-isoxazolyl)-urea and 4-chlorine-6,7-dimethoxy quinolin as raw materials, reacting under the alkaline condition to obtain an intermediate product 4-[(4-amino-3-chlorophenol)-oxy]-6,7-dimethoxy quinolin, and reacting with 3-amino-5-methylisoxazole and N,N'-carbonyldiimidazole, to obtain a target product of the Tivozanib. Compared with the prior art, the preparation method has the beneficial effect. The used raw materials in the preparation process are easily obtained, the prepared Tivozanib has high purity (more than 99.65%) and the most of the contained impurities are the raw materials in the preparation process. the ingredients are clear relatively, and there are less harmful by-products.

A new and practical synthesis of tivozanib

Zhu, Chunping,Mao, Yongjun,Wang, Han,Xu, Jingli

, p. 1882 - 1887 (2016/11/06)

New and improved synthetic route of tivozanib is described on a hectogram scale. An reduction cyclization process to prepare the key intermediate 6,7-dimethoxyquinolin-4-ol from the 3-(dimethylamino)-1-(2-nitrophenyl)prop-2-en-1-one compound at H2/Ni cond

SUBSTITUTED QUINOLINE COMPOUNDS AND METHODS OF USE

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, (2014/01/07)

The present invention provides novel substituted quinoline compounds, pharmaceutical acceptable salts and formulations thereof useful in modulating the protein tyrosine kinase activity, and in modulating cellular activities such as proliferation, differentiation, apoptosis, migration and invasion. The invention also provides pharmaceutically acceptable compositions comprising such compounds and methods of using the compositions in the treatment of hyperproliferative disorders in mammals, especially humans.

Novel potent orally active selective VEGFR-2 tyrosine kinase inhibitors: Synthesis, structure-activity relationships, and antitumor activities of N-phenyl-N′-{4-(4-quinolyloxy)phenyl}ureas

Kubo, Kazuo,Shimizu, Toshiyuki,Ohyama, Shin-Ichi,Murooka, Hideko,Iwai, Akemi,Nakamura, Kazuhide,Hasegawa, Kazumasa,Kobayashi, Yoshiko,Takahashi, Noriko,Takahashi, Kazumi,Kato, Shinichiro,Izawa, Toshio,Isoe, Toshiyuki

, p. 1359 - 1366 (2007/10/03)

N-Phenyl-N′-{4-(4-quinolyloxy)phenyl}ureas were found to be a novel class of potent inhibitors for the vascular endothelial growth factor receptor 2 (VEGFR-2) tyrosine kinase through synthetic modifications of a lead compound and structure-activity relationship studies. A representative compound 6ab, termed Ki8751, inhibited VEGFR-2 phosphorylation at an IC50 value of 0.90 nM, and also inhibited the PDGFR family members such as PDGFRα and c-Kit at 67 nM and 40 nM, respectively. However, 6ab did not have any inhibitory activity against other kinases such as EGFR, HGFR, InsulinR and others even at 10000 nM. 6ab suppressed the growth of the VEGF-stimulated human umbilical vein endothelial cell (HUVEC) on a nanomolar level. 6ab showed significant antitumor activity against five human tumor xenografts such as GL07 (glioma), St-4 (stomach carcinoma), LC6 (lung carcinoma), DLD-1 (colon carcinoma) and A375 (melanoma) in nude mice and also showed complete tumor growth inhibition with the LC-6 xenograft in nude rats following oral administration once a day for 14 days at 5 mg/kg without any body weight loss.

N-[2-CHLORO-4-(6,7-DIMETHOXY-4-QUINOLYL)OXY]PHENYL]-N'-(5-METHYL-3-ISOXAZOLYL)UREA SALT IN CRYSTALLINE FORM

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Page/Page column 19, (2010/02/13)

The present invention provides a crystal of a pharmaceutically acceptable salt of N-{2-chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N'-(5-m ethyl-3-isoxazolyl) urea. This crystal of salt is usable for the therapy of a disease selected from the group consisting of tumors, diabetic retinopathy, chronic rheumatism, psoriasis, atherosclerosis, Kaposi's sarcoma, and exudation type age-related maculopathy, and has characteristics suitable for applications of oral pharmaceutical preparations.

QUINOLINE DERIVATIVES AND QUINAZOLINE DERIVATIVES

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, (2008/06/13)

An object of the present invention is to provide compounds which have antitumor activity and do not change cytomorphosis. Disclosed are compounds represented by formula (I) and a pharmaceutically acceptable salts and solvates thereof and pharmaceutical compositions comprising said compounds: wherein X and Z each independently represent CH or N; R1 to R3 represent H, substituted alkoxy, unsubstituted alkoxy or the like; R4 represents H; R5 to R8 represent H, halogen, alkyl, alkoxy, alkylthio, nitro, or amino, provided that R5 to R8 do not simultaneously represent H; R9 and R10 represent H, alkyl, or alkylcarbonyl; and R11 represents alkyl, alkenyl, alkynyl, or aralkyl.

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