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
• Article Data: 61

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

Description

3,4-Dihydro-7-methoxy-4-oxoquinazolin-6-yl acetate is a brown solid powder with potent inhibitory activity against VEGFR-2/HDAC and a human breast cancer cell line MCF-7.

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 
• 13794-72-4 6,7-dimethoxy-4-hydroxyquinazoline 
• 13790-39-1 6,7-dimethoxy-4-chloroquinazoline 
• 26791-93-5 methyl 4,5-dimethoxy-2-nitrobenzoate 
• 4998-07-6 4,5-dimethoxy-2-nitro-benzoic acid 
• 179688-52-9 4,6-dihydroxy-7-methoxyquinazoline 
• 75-36-5 acetyl chloride 
• 179688-52-9 6-hydroxy-7-methoxy-quinazoline-4-one 
• 31839-20-0 5-hydroxy-4-methoxy-2-nitrobenzoic acid 
• 20357-25-9 6-nitroveratraldehyde 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 31839-21-1 2-amino-5-hydroxy-4-methoxybenzoic acid 
• 57535-57-6 methyl 3-(benzyloxy)-4-methoxy-benzoate 

Downstream Products

• 230955-75-6 6-acetoxy-4-chloro-7-methoxyquinazoline 
• 808793-55-7 3-benzyl-3,4-dihydro-4-oxo-6-acetyloxy-7-methoxy-quinazoline 
• 1389355-33-2 N-(3-bromophenyl)-6-(2-[18F]fluoroethoxy)-7-methoxyquinazolin-4-amine 
• 740081-22-5 4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl acetate 
• 1626387-80-1 (R)-4-((3-chloro-2-fluorophenyl)amino)-7-methoxyquinazolin-6-yl-2,4-dimethylpiperazinyl-1-carboxylic acid ester 
• 1626387-81-2 4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl (2R)-2,4-dimethylpiperazine-1-carboxylate hydrochloride 
• 1626387-80-1 4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl (2S)-2,4-dimethylpiperazine-1-carboxylate 
• 1626387-80-1 4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl (±)-2,4-dimethylpiperazine-1-carboxylate 
• 612501-81-2 tert-butyl 4-((4-((3-chloro-2-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy)piperidine-1-carboxylate 
• 612500-78-4 N-(3-chloro-2-fluorophenyl)-7-methoxy-6-(piperidin-4-yloxy)quinazolin-4-amine 
• 848942-61-0 Sapitinib 
• 1456621-48-9 N¹,N¹-bis(2-chloroethyl)-N⁴-(7-methoxy-6-(3-morpholinopropoxy)quinazolin-4-yl)benzene-1,4-diamine 
• 1456621-47-8 N¹,N¹-bis(2-chloroethyl)-N³-(7-methoxy-6-(3-morpholinopropoxy)quinazolin-4-yl)benzene-1,3-diamine 

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.

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.