179688-53-0

Basic information

• Product Name: 3,4-Dihydro-7-methoxy-4-oxoquinazolin-6-yl acetate
• Synonyms: 7-Methoxy-4-oxo-1,4-dihydroquinazolin-6-yl acetate;6-Acetoxy-7-methoxy-3H-quinazolin-4-one;4-hydroxy-7-methoxyquinazolin-6-yl acetate;6-methoxy-4-oxo-3,4-dihydroquinazolin-7-yl acetate;(7-methoxy-4-oxo-1H-quinazolin-6-yl) acetate;Gefitinib Impurity 3;6-acetoxy-7-methoxy-3,4-dihydroquinazolin-4(3H)-one;6-Acetoxy-7-methoxy-3H-quinazolin-4-one
• CAS NO: 179688-53-0
• Molecular Formula: C₁₁H₁₀N₂O₄
• Molecular Weight: 234.21
• EINECS: 1308068-626-2
• Mol File: 179688-53-0.mol

Chemical Properties

• Melting Point: 293 °C
• Boiling Point: 390.518 °C at 760 mmHg
• Flash Point: 189.979 °C
• Appearance: /
• Density: 1.39
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.612
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 0.67±0.20(Predicted)
• CAS DataBase Reference: 3,4-Dihydro-7-methoxy-4-oxoquinazolin-6-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dihydro-7-methoxy-4-oxoquinazolin-6-yl acetate(179688-53-0)
• EPA Substance Registry System: 3,4-Dihydro-7-methoxy-4-oxoquinazolin-6-yl acetate(179688-53-0)

Safety Data

• Hazardous Substances Data: 179688-53-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dihydro-7-methoxy-4-oxoquinazolin-6-yl acetate is used as a pharmaceutical compound for its potent inhibitory activity against VEGFR-2/HDAC and human breast cancer cell line MCF-7, making it a potential candidate for cancer treatment and therapy.

InChI:InChI=1/C11H10N2O4/c1-6(14)17-10-3-7-8(4-9(10)16-2)12-5-13-11(7)15/h3-5H,1-2H3,(H,12,13,15)

Upstream product

• 108-24-7 acetic anhydride 
• 13794-72-4 3H-6,7-dimethoxyquinazolin-4-one 
• 179688-52-9 6-hydroxy-7-methoxyquinazolin-4(3H)-one 
• 26759-46-6 methyl 2-amino-4,5-dimethoxybenzoate 
• 64-19-7 acetic acid 
• 20323-74-4 2-carboethoxy-4,5-dimethoxyaniline 
• 100905-33-7 ethyl 2-nitro-4,5-dimethoxybenzoate 
• 3943-77-9 ethyl veratrate 
• 93-07-2 Veratric acid 
• 5653-40-7 2-Amino-4,5-dimethoxybenzoic acid 
• 26791-93-5 methyl 4,5-dimethoxy-2-nitrobenzoate 
• 13790-39-1 6,7-dimethoxy-4-chloroquinazoline 
• 164161-49-3 methyl 5-(benzyloxy)-4-methoxy-2-nitrobenzoate 
• 50413-44-0 methyl 2-amino-5-hydroxy-4-methoxybenzoate 

Downstream Products

• 230955-75-6 6-acetoxy-4-chloro-7-methoxyquinazoline 
• 179688-54-1 4-chloro-7-methoxyquinazolin-6-yl acetate hydrochloride salt 
• 184475-71-6 4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline 
• 184475-35-2 gefitinib 
• 808793-55-7 3-benzyl-3,4-dihydro-4-oxo-6-acetyloxy-7-methoxy-quinazoline 
• 16064-15-6 6,7-dihydroxyquinazolin-4(3H)-one 
• 808793-56-8 3-benzyl-6-hydroxy-7-methoxy-3H-quinazolin-4-one 
• 941598-33-0 3-benzyl-3,4-dihydro-4-oxo-6-{cis-4-[N-(tert-butyloxycarbonyl)-N-methyl-amino]-cyclohexyl-oxy}-7-methoxy-quinazoline 
• 941598-41-0 3,4-dihydro-4-oxo-6-[cis-4-(N-morpholinocarbonyl-N-methyl-amino)-cyclohexyl-oxy]-7-methoxy-quinazoline 
• 941598-34-1 3-benzyl-3,4-dihydro-4-oxo-6-[cis-4-(N-morpholinocarbonyl-N-methyl-amino)-cyclohexyl-oxy]-7-methoxy-quinazoline 
• 1024015-16-4 4-[(3-chloro-2-fluoro-phenyl)amino]-6-[cis-4-(N-morpholinocarbonyl-N-methyl-amino)-cyclohexyl-oxy]-7-methoxy-quinazoline 
• 1046137-42-1 4-[(3-chloro-2-fluoro-phenyl)amino]-6-(4-oxo-cyclohexyloxy)-7-methoxy-quinazoline 
• 1046452-35-0 3-benzyl-3,4-dihydro-4-oxo-6-(1,4-dioxa-spiro[4,5]decan-8-yl-oxy)-7-methoxy-quinazoline 

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.

Polysubstituted quinazoline compound and application thereof

The invention discloses a polysubstituted quinazoline compound and an application thereof, and belongs to the field of chemical medicines. The substituted quinazoline compound represented by the general formula (I) and the pharmaceutically acceptable salt thereof have excellent brain barrier permeability, enhanced metabolic stability and longer metabolic half-life period, show higher inhibitory activity on an activated or drug-resistant mutant form EGFR than a wild type EGFR, and can effectively reduce side effects.

QUINOLINE AND QUINAZOLINE COMPOUNDS AND METHODS OF USE THEREOF

Compounds and methods for their preparation and use as therapeutic or prophylactic agents, fo example for treatment of cancer, bacterial or viral diseases by targeting Ectonucleotide Pyrophosphatase/Phosphodiesterase- 1 (ENPP1).

INHIBITORS OF MUTANT EGFR FAMILY TYROSINE-KINASES

An epidermal growth factor receptor (EGFR) family tyrosine kinase inhibitor comprising a functional group that can bind to the serine S797 residue in EGFR having a C797S mutation or the serine S805 residue in HER2 having a C805S mutation.

Absolute Binding Free Energy Calculation and Design of a Subnanomolar Inhibitor of Phosphodiesterase-10

Accurate prediction of absolute protein-ligand binding free energy could considerably enhance the success rate of structure-based drug design but is extremely challenging and time-consuming. Free energy perturbation (FEP) has been proven reliable but is limited to prediction of relative binding free energies of similar ligands (with only minor structural differences) in binding with a same drug target in practical drug design applications. Herein, a Gaussian algorithm-enhanced FEP (GA-FEP) protocol has been developed to enhance the FEP simulation performance, enabling to efficiently carry out the FEP simulations on vanishing the whole ligand and, thus, predict the absolute binding free energies (ABFEs). Using the GA-FEP protocol, the FEP simulations for the ABFE calculation (denoted as GA-FEP/ABFE) can achieve a satisfactory accuracy for both structurally similar and diverse ligands in a dataset of more than 100 receptor-ligand systems. Further, our GA-FEP/ABFE-guided lead optimization against phosphodiesterase-10 led to the discovery of a subnanomolar inhibitor (IC50 = 0.87 nM, ~2000-fold improvement in potency) with cocrystal confirmation.

A preparation method of gefitinib (by machine translation)

The present invention relates to organic chemical and medical technology field, in particular relates to a preparation method of gefitinib. The present invention provides a preparation method of gefitinib, obtained by formula I compounds, the formula I compound preparation method comprises the following steps: nitration reaction, oxidation reaction, selective demethylation reaction, reduction reaction, a cyclization reaction, phenolic hydroxyl acetylation reaction. The present invention provides a preparation method can at the same time reducing the cost, it is easy for the refined purification, easy preparation and control of related impurities, the overall preparation process routes are greatly optimized, is suitable for industrial scale production. (by machine translation)

Quinazoline derivatives and its preparation method and application

The invention relates to quinazoline derivatives and its preparation method and application. The quinazoline derivatives with The structural formula, the quinazoline derivative to gefitinib for the positive control, the result shows that compared with the gefitinib has good activity; and lead compound OTS514 compared, equivalent activity, PBK/TOPK inhibitors for further transformation and the discovery of new anti-tumor medicine phenological shopping has higher learning with the reference value. The invention also provides a preparation method of the quinazoline derivatives and the preparation of PBK/TOPK inhibitor and an anticancer drug.

A 3, 4 - dihydro -7 - methoxy -4 - [...] -6 - ethoxylate ester preparation method (by machine translation)

The present invention relates to organic chemical and medical technology field, in particular to a 3, 4 - dihydro - 7 - methoxy - 4 - [...] - 6 - ethoxylate ester preparation method. The present invention provides a gefitinib 3, 4 - dihydro - 7 - methoxy - 4 - [...] - 6 - ethoxylate ester preparation method comprises the following steps: nitration reaction, oxidation reaction, selective demethylation reaction, reduction reaction, a cyclization reaction, phenolic hydroxyl acetylation reaction. Preparation method provided by the invention can at the same time reducing the cost, it is easy for the refined purification, easy preparation and control of related impurities, the overall preparation process routes are greatly optimized, is suitable for industrial scale production. (by machine translation)

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.

AN IMPROVED PROCESS FOR THE PREPARATION OF N-(3-ETHYNYLPHENYL)-7-METHOXY-6-(3-MORPHOLINOPROPOXY) QUINAZOLIN -4-AMINE DIHYDROCHLORIDE

Present invention relates to an improved process for the preparation of N-(3- ethynylphenyl)-7-methoxy-6-(3-morpholinopropoxy) quinazolin-4-amine dihydrochloride of formula-I.