153437-78-6

Basic information

• Product Name: N-(3-chloro-4-fluorophenyl)-6 ,7-dimethoxyquinazolin-4-amine
• Synonyms: Gefitinib Impurity 2
• CAS NO: 153437-78-6
• Molecular Formula: C16H13ClFN3O2
• Molecular Weight: 333.74
• Mol File: 153437-78-6.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(3-chloro-4-fluorophenyl)-6 ,7-dimethoxyquinazolin-4-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-chloro-4-fluorophenyl)-6 ,7-dimethoxyquinazolin-4-amine(153437-78-6)
• EPA Substance Registry System: N-(3-chloro-4-fluorophenyl)-6 ,7-dimethoxyquinazolin-4-amine(153437-78-6)

Safety Data

• Hazardous Substances Data: 153437-78-6(Hazardous Substances Data)

Usage

Description

N-(3-chloro-4-fluorophenyl)-6,7-dimethoxyquinazolin-4-amine is an anilinoquinazoline derivative with a unique chemical structure that features a 3-chloro-4-fluorophenyl group attached to a quinazolin-4-amine core. N-(3-chloro-4-fluorophenyl)-6
,7-dimethoxyquinazolin-4-amine possesses potential biological activities and can be utilized in various applications due to its ability to inhibit specific enzymes and interact with biological targets.

Uses

Used in Pharmaceutical Industry:
N-(3-chloro-4-fluorophenyl)-6,7-dimethoxyquinazolin-4-amine is used as an inhibitor of tyrosine kinases for its potential therapeutic applications in cancer treatment. The compound acts as an allosteric inhibitor of the enzyme frutose 1,6-bisphosphatase, which plays a crucial role in cellular metabolism and has been implicated in various diseases, including cancer.
Used in Drug Design and Development:
N-(3-chloro-4-fluorophenyl)-6,7-dimethoxyquinazolin-4-amine serves as a lead compound for further drug design and development. Its unique chemical structure and biological activities make it a promising candidate for the development of novel therapeutic agents targeting tyrosine kinases and other related enzymes. Researchers can use this compound as a starting point to design more potent and selective inhibitors with improved pharmacological properties.
Used in Research and Development:
In the field of research and development, N-(3-chloro-4-fluorophenyl)-6,7-dimethoxyquinazolin-4-amine can be employed as a tool compound to study the role of tyrosine kinases and frutose 1,6-bisphosphatase in various biological processes and disease pathways. N-(3-chloro-4-fluorophenyl)-6
,7-dimethoxyquinazolin-4-amine can help researchers gain a better understanding of the molecular mechanisms underlying these processes and identify potential therapeutic targets for the development of new drugs.

Upstream product

• 367-21-5 3-chloro-4-fluorophenylamine 
• 13790-39-1 6,7-dimethoxy-4-chloroquinazoline 
• 26759-46-6 methyl 2-amino-4,5-dimethoxybenzoate 
• 13794-72-4 3H-6,7-dimethoxyquinazolin-4-one 
• 16078-71-0 ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate 
• 5334-48-5 4-chloro-1-(phenyl)-1H-pyrazolo[3,4-d]pyrimidine 

Downstream Products

• 184475-71-6 4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline 

Relevant articles and documents

Synthesis, biological evaluation and molecular modelling studies of 4-anilinoquinazoline derivatives as protein kinase inhibitors

A series of novel 4-anilinoquinazoline derivatives (3a-3j) has been synthesized and evaluated as potential inhibitors for protein kinases implicated in Alzheimer's disease. Among all the synthesized compounds, compound 3e (N-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazolin-4-amine) exhibited the most potent inhibitory activity against CLK1 and GSK-3α/β kinase with IC50 values of 1.5 μM and 3 μM, respectively. Docking studies were performed to elucidate the binding mode of the compounds to the active site of CLK1 and GSK-3β. The results of our study suggest that compound 3e may serve as a valuable template for the design and development of dual inhibitors of CLK1 and GSK-3α/β enzymes with potential therapeutic application in Alzheimer's disease.

Method suitable for industrial production and preparation of gefitinib

The invention discloses a method suitable for industrial production and preparation of gefitinib, which takes 6, 7-dimethoxy-3H-quinazoline-4-one as a raw material, and gefitinib is obtained through four steps of chlorination, amination, demethylation and reaction with N-(3-chloropropyl) morpholine, so as to solve the problems that the existing synthetic route is complex and long, the total yield is low, a large number of environment-unfriendly reagents are used, and the technology cannot be amplified. According to the method, pyridine hydrochloride/DMSO is utilized to remove 6-position methyl in a high-selectivity manner, a key intermediate N-(3-chloro-4-fluorophenyl)-6-hydroxy-7-methoxyquinazoline-4-amine is obtained in a high yield manner, and convenient synthesis of the intermediate is realized. The synthesis method has the advantages of cheap and easily available raw materials and short route, and gefitinib and derivatives modified by different 6-site groups can be rapidly obtained. The preparation method solves the bottleneck problem of large-scale production of the active pharmaceutical ingredient gefitinib.

Impact of aryloxy-linked quinazolines: A novel series of selective VEGFR-2 receptor tyrosine kinase inhibitors

Three series of 6,7-dimethoxyquinazoline derivatives substituted in the 4-position by aniline, N-methylaniline and aryloxy entities, targeting EGFR and VEGFR-2 tyrosine kinases, were designed and synthesized. Pharmacological activities of these compounds