179552-75-1

Basic information

• Product Name: N-(3-chloro-4-fluorophenyl)-7-Methoxy-6-aminoquinazolin-4-aMine
• Synonyms: N-(3-chloro-4-fluorophenyl)-7-Methoxy-6-aminoquinazolin-4-aMine;N4-(3-Chloro-4-fluorophenyl)-7-methoxyquinazoline-4,6-diamine
• CAS NO: 179552-75-1
• Molecular Formula: C₁₅H₁₂ClFN₄O
• Molecular Weight: 318.7333832
• EINECS: -0
• Mol File: 179552-75-1.mol

Chemical Properties

• Boiling Point: 487.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.458±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 6.03±0.30(Predicted)
• CAS DataBase Reference: N-(3-chloro-4-fluorophenyl)-7-Methoxy-6-aminoquinazolin-4-aMine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-chloro-4-fluorophenyl)-7-Methoxy-6-aminoquinazolin-4-aMine(179552-75-1)
• EPA Substance Registry System: N-(3-chloro-4-fluorophenyl)-7-Methoxy-6-aminoquinazolin-4-aMine(179552-75-1)

Safety Data

• Hazardous Substances Data: 179552-75-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-(3-chloro-4-fluorophenyl)-7-Methoxy-6-aminoquinazolin-4-aMine is used as a potential therapeutic agent for its possible kinase inhibition properties, which can be beneficial in the treatment of various diseases where kinase activity is dysregulated.
Used in Oncology:
In the field of oncology, N-(3-chloro-4-fluorophenyl)-7-Methoxy-6-aminoquinazolin-4-aMine is used as a potential anti-cancer agent. Its structural features may allow it to interact with cellular targets, potentially leading to the inhibition of cancer cell growth and proliferation.
Further research and development are necessary to fully understand the pharmacological properties and explore the potential therapeutic uses of N-(3-chloro-4-fluorophenyl)-7-Methoxy-6-aminoquinazolin-4-aMine in various medical applications.

Upstream product

• 1012057-48-5 N-(3-chloro-4-fluorophenyl)-7-methoxy-6-nitroquinazolin-4-amine hydrochloride 
• 179552-74-0 N-(3-chloro-4-fluorophenyl)-7-methoxy-6-nitroquinazolin- 4-amine 
• 162012-67-1 N-(3-chloro-4-fluorophenyl)-7-fluoro-6-nitroquinazolin-4-amine 
• 162012-69-3 7-fluoro-6-nitro-3H-quinazolin-4-one 
• 162012-70-6 4-chloro-7-fluoro-6-nitroquinazoline 
• 31374-18-2 7-chloro-3,4-dihydroquinazolin-4-one 
• 367-21-5 3-chloro-4-fluorophenylamine 
• 162012-69-3 7-fluoro-6-nitro-4-hydroxyquinazoline 
• 53449-14-2 7-chloro-6-nitro-4(3H)-quinazolinone 
• 89-77-0 2-Amino-4-chlorobenzoic acid 
• 1012057-47-4 7-methoxy-6-nitroquinazolin-4(3H)-one 
• 55496-69-0 4-chloro-7-methoxy-6-nitroquinazoline 
• 16499-57-3 7-fluoro-3H-quinazolin-4-one 
• 446-32-2 4-fluoroanthranilic acid 

Downstream Products

• 1012057-49-6 methyl 3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-ylcarbamoyl)butanoate 
• 1012920-25-0 C₁₅H₁₀ClFIN₃O 
• 1414884-63-1 (E)-N-[4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yl]-4-[2-azaspiro[ 3.4]octan-2-yl]-2-butenamide 
• 1012054-73-7 N₁-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yl)-N₅-hydroxyglutaramide 

Relevant articles and documents

Industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles-catalyzed hydrogenation of nitroarenes

The development of green and efficient methods for hydrogenation of nitroarenes is still highly demanding in organic synthesis. Herein, we report an industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles process for the synthesis of aryl amines with good yields via hydrogenation of nitroarenes. Nine key anti-cancer drug intermediates were successfully achieved with protocol. And Osimertinib intermediate 4m can be smoothly synthesized at a 2.67 kg-scale with >99.5% HPLC purity. This protocol features cheap carbon source, highly catalytic activity, simple operation, kilogram-scalable and recyclable catalysts (eight times without observable losing activity).

Preparation method of dacotinib

The present invention discloses a method of preparation of dacotinib, comprising the following steps: (N- (3-chloro-4-fluorophenyl) -7-fluoro-6-nitro-4-quinazoline) in a base / methanol system to undergo a methyl oxidation reaction, to compound 02 (N- (3-

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Tyrosine kinase inhibitor and pharmaceutical application thereof

The invention relates to a tyrosine kinase inhibitor containing a quinazoline derivative in the fields of tumor treatment medicines and the like, and application of the tyrosine kinase inhibitor in treatment medicines for inhibiting and treating diseases caused by overexpression of tyrosine kinase. The active ingredient of the tyrosine kinase inhibitor is a quinazoline derivative with a structure shown in the following formula: a functional group containing XCH2 (CH2) nC = O is introduced on the basis of a quinazoline structure, and the functional group is easily combined with cysteine sulfydryl through nucleophilic reaction to form a covalent bond so that the activity of tyrosine kinase is irreversibly inhibited.

STEFs: Activated Vinylogous Protein-Reactive Electrophiles

Reported here is the synthesis of a class of semi-oxamide vinylogous thioesters, designated STEFs, and the use of these agents as new electrophilic warheads. This work includes preparation of simple probes that contain this reactive motif as well as its installation on a more complex kinase inhibitor scaffold. A key aspect of STEFs is their reactivity towards both thiol and amine groups. Shown here is that amine conjugations in peptidic and proteinogenic samples can be facilitated by initial, fast conjugation to proximal thiol residues. Evidence that both the selectivity and the reactivity can be tuned by the structure of STEFs is provided, and given the unique ability of this functionality to conjugate by an addition-elimination mechanism, STEFs are electrophilic warheads that could find broad use in chemical biology.

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A series of quinazoline derivatives with benzylidene hydrazine carboxamide were designed and synthesised as EGFR inhibitors. Most compounds exhibited exceptional anti-proliferative activity against A549, HepG2, MCF-7 and H1975 cells. Furthermore, six compounds demonstrated excellent inhibition activity against EGFRWT with the IC50 value both less than 2 nM. Among the six compounds, 44 exhibited the strongest activity (0.4 nM) and potently inhibited EGFRL858R/T790M (0.1 μM). Excitingly, the most potent compound 14 showed excellent enzyme inhibitory activity with 6.3 nM and 8.4 nM for both EGFRWT and EGFRT790M/L858R. The result of AO single staining and Annexin V/PI staining showed that the compound 14 and 44 could induce remarkable apoptosis of A549 cells. The compound 14 arrested the cell cycle at the S phase and compound 44 arrested the cell cycle at the G0 phase in A549 cells. These preliminary results demonstrate that compound 14 and 44 may be promising lead compound-targeting EGFR.

EGFR PROTEOLYSIS TARGETING CHIMERIC MOLECULES AND ASSOCIATED METHODS OF USE

The present disclosure relates to bifunctional compounds, which find utility as modulators of receptor tyrosine kinase (RTK) proteins. In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a ligand which binds to an E3 ubiquitin ligase and on the other end a moiety which binds a target protein, such that the target protein is placed in proximity to the ubiquitin ligase to effectuate ubiquitination, and therefore, degradation (and inhibition) of the target protein. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein are treated or prevented with compounds and compositions of the present disclosure.

Novel quinazoline derivatives bearing various 6-benzamide moieties as highly selective and potent EGFR inhibitors

A series of novel quinazoline derivatives bearing various C-6 benzamide substituents were synthesized and evaluated as EGFR inhibitors, and most showed significant inhibitory potency against EGFR kinase. In particular, compound 6g possessed potent inhibitory activity against EGFR wild-type (IC50 = 5 nM), and strong antiproliferative activity against HCC827 and Ba/F3 (L858R) cell lines. Kinase profiling against a panel of 365 kinases showed that 6g was highly selective for EGFR. Furthermore, 6g showed desirable properties in assays of liver microsome metabolic stability and cytochromes P450 inhibition and preliminary pharmacokinetic study. The overall attractive profile of 6g made it an interesting compound for further development.

Design, synthesis, and docking studies of quinazoline analogues bearing aryl semicarbazone scaffolds as potent EGFR inhibitors

Two series of quinazoline derivatives bearing aryl semicarbazone scaffolds (9a–o and 10a–o) were designed, synthesized and evaluated for the IC50 values against four cancer cell lines (A549, HepG2, MCF-7 and PC-3). The selected compound 9o was further evaluated for the inhibitory activity against EGFR kinases. Four of the compounds showed excellent cytotoxicity activity and selectivity with the IC50 values in single-digit μM to nanomole range. Two of them are equal to more active than positive control afatinib against one or more cell lines. The most promising compound 9o showed the best activity against A549, HepG2, MCF-7 and PC-3 cancer cell lines and EGFR kinase, with the IC50 values of 1.32?±?0.38?μM, 0.07?±?0.01?μM, 0.91?±?0.29?μM and 4.89?±?0.69?μM, which were equal to more active than afatinib (1.40?±?0.83?μM, 1.33?±?1.28?μM, 2.63?±?1.06?μM and 3.96?±?0.59?μM), respectively. Activity of the most promising compound 9o (IC50 56?nM) against EGFR kinase was slightly lower to the positive compound afatinib (IC50 1.6?nM) but more active than reference staurosporine (IC50 238?nM). The result of flow cytometry, with the dose of compound 9o increasing, which indicated the compound 9o could induce remarkable apoptosis of A549 and cells in a dose dependent manner. Structure–activity relationships (SARs) and docking studies indicated that replacement of the cinnamamide group by aryl semicarbazone scaffolds slightly decreased the anti-tumor activity. The results suggested that hydroxy substitution at C-4 had a significant impact on the activity and replacement of the tetrahydrofuran group by methyl moiety was not beneficial for the activity.

NOVEL FLUORINATED QUINAZOLINE DERIVATIVES AS EGFR INHIBITORS

A novel class of fluorinated derivatives of Formula (I) have been prepared and found to be useful in the treatment of cancers and other EGFR related disorders. (I)