196603-96-0

Basic information

• Product Name: 4-(4-bromo-2-fluorophenylamino)-6-methoxyquinazolin-7-ol
• Synonyms: 4-(4-bromo-2-fluorophenylamino)-6-methoxyquinazolin-7-ol;4-(4-Bromo-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline;6-Methoxy-7-hydroxy-4-(2''-fluoro-4''-broMoaniline)quinazoline;7-Quinazolinol, 4-[(4-broMo-2-fluorophenyl)aMino]-6-Methoxy-;4-[(4-Bromo-2-fluorophenyl)amino]-6-methoxy-7-Quinazolinol
• CAS NO: 196603-96-0
• Molecular Formula: C₁₅H₁₁BrFN₃O₂
• Molecular Weight: 364
• EINECS: 1806241-263-5
• Mol File: 196603-96-0.mol

Chemical Properties

• Melting Point: 268-270 °C
• Boiling Point: 470.985 °C at 760 mmHg
• Flash Point: 238.643 °C
• Appearance: /
• Density: 1.663
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 5.51±0.40(Predicted)
• CAS DataBase Reference: 4-(4-bromo-2-fluorophenylamino)-6-methoxyquinazolin-7-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-bromo-2-fluorophenylamino)-6-methoxyquinazolin-7-ol(196603-96-0)
• EPA Substance Registry System: 4-(4-bromo-2-fluorophenylamino)-6-methoxyquinazolin-7-ol(196603-96-0)

Safety Data

• Hazardous Substances Data: 196603-96-0(Hazardous Substances Data)

Upstream product

• 14348-41-5 3-bromo-4-hydroxy-benzoic acid 
• 99-96-7 4-hydroxy-benzoic acid 
• 176240-84-9 methyl 4-(benzyloxy)-3-bromobenzoate 
• 124-41-4 sodium methylate 
• 617-05-0 ethyl vanillate 
• 185033-64-1 ethyl 4-benzyloxy-3-methoxybenzoate 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 179688-01-8 7-(benzyloxy)-6-methoxyquinazolin-4(3H)-one 
• 60547-94-6 5-Methoxy-2-nitro-4-(phenylmethoxy)benzamide 
• 2426-84-8 4-(benzyloxy)-5-methoxy-2-nitrobenzaldehyde 

Downstream Products

• 413599-62-9 N-(4-bromo-2-fluorophenyl)-6-methoxy-7-[2-(1H-1,2,3-triazol-1-yl)ethoxy]quinazoline-4-amine 
• 413599-49-2 tert-butyl 4-[2-({4-[(4-bromo-2-fluorophenyl)amino]-6-methylquinazolin-7-yl}oxy)ethyl]piperidine-1-carboxylate 
• 205194-14-5 N-(4-bromo-2-fluorophenyl)-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine 
• 338992-20-4 4-(((4-((4-bromo-2-fluorophenyl)amino)-6-methoxyquinazolin-7-yl)oxy)methyl)piperidine-1-carboxylic acid tert-butyl ester 
• 338992-12-4 N-Desmethylvandetanib 
• 413599-48-1 4-(4-bromo-2-fluoroanilino)-6-methoxy-7-[2-(piperidin-4-yl)ethoxy]quinazoline 
• 867150-30-9 (4R,6S)-{6-[4-(4-bromo-2-fluorophenylamino)-6-methoxyquinazolin-7-yloxymethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-acetic acid ethyl ester 
• 205193-61-9 4-(4-bromo-2-fluoroanilino)-6-methoxy-7-(3-methylthiopropoxy)quinazoline 
• 205193-78-8 4-(4-bromo-2-fluoroanilino)-6-methoxy-7-(3-(2-oxypyrrolidin-1-yl)propoxy)quinazoline hydrochloride 
• 205194-23-6 4-(4-bromo-2-fluoroanilino)-6-methoxy-7-(3-methylaminopropoxy)quinazoline 
• 205193-97-1 4-(4-bromo-2-fluoroanilino)-6-methoxy-7-(2-(3-oxomorpholino)ethoxy)quinazoline hydrochloride 
• 205193-98-2 4-(4-bromo-2-fluoroanilino)-6-methoxy-7-(2-(2-oxopyrrolidin-1-yl)ethoxy)quinazoline hydrochloride 
• 910298-60-1 4-((4-bromo-2-fluorophenyl)amino)-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-6-ol 
• 443913-73-3 vandetanib 

Relevant articles and documents

Design, synthesis and biological evaluation of novel 4-anilinoquinazoline derivatives as hypoxia-selective EGFR and VEGFR-2 dual inhibitors

Tyrosine kinase inhibitors (TKIs) have achieved substantial clinical effects for cancer treatment while causing a number of adverse effects. Since hypoxia is an intrinsic difference between solid tumor and healthy tissues, one strategy to overcome the adverse effects of TKIs is to enhance the specificity of anti-tumor activity by selectively targeting hypoxic region of tumors. Herein, we designed and synthesized a series of novel 4-anilinoquinazoline derivatives by introducing 3-nitro-1,2,4-triazole group to the side chain of vandetanib with modification of aniline moiety. Lead compounds, 10a and 10g, exhibited potent inhibitory activity against EGFR and VEGFR-2 kinase. Moreover, these two compounds were shown to enhance anti-proliferative activities on A549 and H446 cells under hypoxic conditions compared to vandetanib and dramatically down-regulate VEGF gene expression. In vivo studies confirmed that 10a and 10g not only inhibited tumor growth in A549 xenografts of BALB/c-nu mice but also significantly reduce toxicity associated with weight loss compared to vandetanib. These results suggest that EGFR/VEGFR-2 dual inhibitors, 10a and 10g, emerged as potential hypoxia-selective anti-tumor drugs with less toxicity for inhibiting in vitro and in vivo models of non-small cell lung cancer cells.

A where the shall he loni intermediate and its preparation method

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4-Substituted quinazoline derivatives as novel EphA2 receptor tyrosine kinase inhibitors

Erythropoietin-producing hepatocellular receptor tyrosine kinase subtype A2 (EphA2) is an attractive therapeutic target for suppressing tumor progression. In our efforts to discover novel small molecules to inhibit EphA2, a class of compound based on 4-substituted quinazoline containing 7-(morpholin-2-ylmethoxy) group was identified as a novel hit by high throughput screening campaign. Structural modification of parent quinazoline scaffolds by introducing substituents on aniline displayed potent inhibitory activities toward EphA2.

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Synthesis and in vitro evaluation of [18F](R)-FEPAQ: A potential PET ligand for VEGFR2

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Radiosynthesis of [11C]Vandetanib and [11C]chloro- Vandetanib as new potential PET agents for imaging of VEGFR in cancer

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Process for the identification of novel enzyme interacting compounds

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QUINAZOLINE DERIVATIVES AS VEGF INHIBITORS

The invention relates to quinazoline derivatives of the formula I:- wherein: m is an integer from 1 to 3; R 1 represents halogeno or C 1-3 alkyl; X 1 represents -O-; R 2 is selected from one of the following three groups: 1) C 1-5 alkylR 3 (wherein R 3 is piperidin-4-yl which may bear one or two substituents selected from hydroxy, halogeno, C 1-4 alkyl, C 1-4 hydroxyalkyl and C 1-4 alkoxy; 2) C 2-5 alkenylR 3 (wherein R 3 is as defined hereinbefore); 3) C 2-5 alkynylR 3 (wherein R 3 is as defined hereinbefore); and wherein any alkyl, alkenyl or alkynyl group may bear one or more substituents selected from hydroxy, halogeno and amino; and salts thereof; processes for their preparation, pharmaceutical compositions containing a compound of formula I or a pharmaceutically acceptable salt thereof as active ingredient. The compounds of formula I and the pharmaceutically acceptable salts thereof inhibit the effects of VEGF, a property of value in the treatment of a number of disease states including cancer and rheumatoid arthritis.