740081-22-5

Basic information

• Product Name: 4-((3-chloro-2-fluorophenyl)amino)-7-methoxyquinazolin-6-yl acetate
• Synonyms: 4-((3-chloro-2-fluorophenyl)amino)-7-methoxyquinazolin-6-yl acetate;6-Quinazolinol, 4-[(3-chloro-2-fluorophenyl)amino]-7-methoxy-, 6-acetate;6-acetoxy-4-(3-chloro-2-fluoroanilino)-7-methoxyquinazoline
• CAS NO: 740081-22-5
• Molecular Formula: C₁₇H₁₃ClFN₃O₃
• Molecular Weight: 361.7548232
• Mol File: 740081-22-5.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 454.4±45.0 °C(Predicted)
• Appearance: /
• Density: 1.425±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 5.22±0.30(Predicted)
• CAS DataBase Reference: 4-((3-chloro-2-fluorophenyl)amino)-7-methoxyquinazolin-6-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-((3-chloro-2-fluorophenyl)amino)-7-methoxyquinazolin-6-yl acetate(740081-22-5)
• EPA Substance Registry System: 4-((3-chloro-2-fluorophenyl)amino)-7-methoxyquinazolin-6-yl acetate(740081-22-5)

Safety Data

• Hazardous Substances Data: 740081-22-5(Hazardous Substances Data)

Usage

Description

4-((3-chloro-2-fluorophenyl)amino)-7-methoxyquinazolin-6-yl acetate is a chemical compound with a complex structure, characterized by its chloro and fluoro substitutions on the phenyl ring, as well as its quinazolin-6-yl and acetate functional groups. 4-((3-chloro-2-fluorophenyl)amino)-7-methoxyquinazolin-6-yl acetate is likely to have specific properties and reactivity due to its unique molecular structure, making it a potential candidate for various applications in the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Industry:
4-((3-chloro-2-fluorophenyl)amino)-7-methoxyquinazolin-6-yl acetate is used as a pharmaceutical intermediate for the synthesis of various therapeutic agents. Its unique structure and functional groups make it a valuable building block in the development of new drugs, particularly those targeting specific biological receptors or enzymes.
Used in Chemical Research:
In the field of chemical research, 4-((3-chloro-2-fluorophenyl)amino)-7-methoxyquinazolin-6-yl acetate can be employed as a starting material or a key intermediate in the synthesis of novel compounds with potential applications in various industries. Its reactivity and structural features may allow for the development of new chemical entities with improved properties or functions.
Used in Drug Synthesis:
As a key intermediate in the synthesis of AZD3759, a novel epidermal growth factor receptor (EGFR) tyrosine kinase inhibitor (TKI), 4-((3-chloro-2-fluorophenyl)amino)-7-methoxyquinazolin-6-yl acetate plays a crucial role in the development of new antitumor drugs. Its incorporation into the final drug molecule may contribute to the compound's ability to penetrate the central nervous system and exhibit promising antitumor effects on non-small cell lung cancer (NSCLC). Further research is needed to understand the regulatory effects of this inhibitor on the antitumor efficacy of radiation (RA).

Upstream product

• 2106-04-9 3-chloro-2-fluoroaniline 
• 230955-75-6 6-acetoxy-4-chloro-7-methoxyquinazoline 
• 13794-72-4 3H-6,7-dimethoxyquinazolin-4-one 
• 179688-52-9 6-hydroxy-7-methoxyquinazolin-4(3H)-one 
• 179688-53-0 (4-hydroxy-7-methoxyquinazolin-6-yl) acetate 
• 4998-07-6 4,5-dimethoxy-2-nitro-benzoic acid 
• 31839-20-0 5-hydroxy-4-methoxy-2-nitrobenzoic acid 
• 31839-21-1 2-amino-5-hydroxy-4-methoxybenzoic acid 
• 26791-93-5 methyl 4,5-dimethoxy-2-nitrobenzoate 
• 100905-33-7 ethyl 2-nitro-4,5-dimethoxybenzoate 
• 26759-46-6 methyl 2-amino-4,5-dimethoxybenzoate 
• 20323-74-4 2-carboethoxy-4,5-dimethoxyaniline 

Downstream Products

• 848440-15-3 4-(3-chloro-2-fluoroanilino)-6,7-dihydroxyquinazoline 
• 870152-50-4 4-(3-chloro-2-fluoro-phenylamino)-7-isopropoxy-quinazolin-6-ol 
• 848440-16-4 acetic acid 4-(3-chloro-2-fluoro-phenylamino)-7-hydroxy-quinazolin-6-yl ester 
• 870152-49-1 4-(3-chloro-2-fluoro-phenylamino)-7-(2-methylsulfanyl-ethoxy)-quinazolin-6-ol 
• 870152-48-0 4-(3-chloro-2-fluoro-phenylamino)-7-(2-methoxy-ethoxy)-quinazolin-6-ol 
• 870152-43-5 2,2-dimethyl-propionic acid 4-(3-chloro-2-fluoro-phenylamino)-7-hydroxy-quinazolin-6-yl ester 
• 870152-47-9 2,2-dimethyl-propionic acid 4-(3-chloro-2-fluoro-phenylamino)-7-isopropoxy-quinazolin-6-yl ester 
• 870152-46-8 2,2-dimethyl-propionic acid 4-(3-chloro-2-fluoro-phenylamino)-7-(2-methylsulfanyl-ethoxy)-quinazolin-6-yl ester 
• 870152-45-7 2,2-dimethyl-propionic acid 4-(3-chloro-2-fluoro-phenylamino)-7-(2-methoxy-ethoxy)-quinazolin-6-yl ester 

Relevant articles and documents

Design, synthesis and biological evaluation of sulfamoylphenyl-quinazoline derivatives as potential EGFR/CAIX dual inhibitors

Multi-target, especially dual-target, drug design has become a popular research field for cancer treatment. Development of small molecule dual-target inhibitors through hybridization strategy can provide highly potent and selective anticancer agents. In this study, three series of quinazoline derivatives bearing a benzene-sulfonamide moiety were designed and synthesized as dual EGFR/CAIX inhibitors. All the synthesized compounds were evaluated against epidermoid carcinoma (A431) and non-small cell lung cancer (A549 and H1975) cell lines, which displayed weak to potent anticancer activity. In particular, compound 8v emerged as the most potent derivative against mutant-type H1975 cells, which exhibited comparable activity to osimertinib. Importantly, 8v exhibited stronger anti-proliferative activity than osimertinib against H1975 cells under hypoxic condition. Kinase inhibition studies indicated that 8v showed excellent inhibitory effect on EGFRT790M enzyme, which was 41 times more effective than gefitinib and almost equal to osimertinib. Mechanism studies revealed that 8v exhibited remarkable CAIX inhibitory effect comparable to acetazolamide and significantly inhibited the expression of p-EGFR as well as its downstream p-AKT and p-ERK in H1975 cells. Notably, 8v was found to inhibit the expression of CAIX and its upstream HIF-1α in H1975 cells under hypoxic condition. Molecular docking was also performed to gain insights into the ligand-binding interactions of 8v inside EGFRWT, EGFRT790M and CAIX binding sites.

COMPOSITIONS AND METHODS FOR TREATING CANCER

The present disclosure relates to compounds that are capable penetrating to the blood brain barrier to modulate the activity of EGFR tyrosine kinase. The disclosure further relates to methods of treating Glioblastoma and other EGFR mediated cancers. The disclosure further relates to methods of treating Glioblastoma and other EGFR mediated cancers that have been determined to have altered glucose metabolism in the presence of inhibitors. The present disclosure also provides methods of administering to a subject a glucose metabolism inhibitor and a cytoplasmic p53 stabilizer.

Preparation method of targeted drug AZD3759 intermediate

The invention discloses a preparation method of a targeted drug AZD3759 intermediate, which comprises the following steps of: firstly, 6-nitro veratric acid is hydrolyzed under alkaline conditions toobtain 2-nitro-4-methoxy-5-hydroxybenzoic acid, the 2-nitro-4-methoxy-5-hydroxybenzoic acid is then reduced by hydrazine hydrate under the action of catalyst ferric chloride hexahydrate activated carbon mixture to obtain 2-amino-4-methoxy-5-hydroxybenzoic acid, 2-amino-4-methoxy-5-hydroxybenzoic acid is reacted with formamidine acetate to obtain 4,6-dihydroxy-7-methoxyquinazoline, 4,6-dihydroxy-7-methoxyquinazoline is reacted with acetyl chloride under alkaline conditions to obtain 4-hydroxyl-6-acetoxy-7-methoxyquinazoline, finally 4-hydroxyl-6-acetoxy-7-methoxyquinazoline is reacted with 3-chlorine-2-fluoroaniline by Mitsunobu reaction under the action of triphenylphosphine and azo reagent to obtain 4-[(3-chloro-2-fluorophenyl)amino]-6-acetoxy-7-methoxyquinazoline. The invention reduces the synthesis steps, reduces the use of harmful compounds, reduces the production cost and optimizes the production operation.