230955-75-6

Basic information

• Product Name: 6-Quinazolinol,4-chloro-7-methoxy-, 6-acetate
• Synonyms: 6-Quinazolinol,4-chloro-7-methoxy-, acetate (ester) (9CI);4-Chloro-6-acetoxy-7-methoxyquinazoline;4-Chloro-6-methylcarbonyloxy-7-methoxyquinazoline;4-Chloro-7-methoxyquinazolin-6-yl acetate;6-Acetoxy-4-chloro-7-methoxyquinazoline;Acetic acid4-chloro-7-methoxyquinazolin-6-yl ester
• CAS NO: 230955-75-6
• Molecular Formula: C₁₁H₉ClN₂O₃
• Molecular Weight: 252.6538
• EINECS: 1308068-626-2
• Mol File: 230955-75-6.mol
• Article Data: 78

Chemical Properties

• Boiling Point: 364.609 °C at 760 mmHg
• Flash Point: 174.309 °C
• Appearance: /
• Density: 1.376 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.605
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 0.50±0.30(Predicted)
• CAS DataBase Reference: 6-Quinazolinol,4-chloro-7-methoxy-, 6-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Quinazolinol,4-chloro-7-methoxy-, 6-acetate(230955-75-6)
• EPA Substance Registry System: 6-Quinazolinol,4-chloro-7-methoxy-, 6-acetate(230955-75-6)

Safety Data

• Hazardous Substances Data: 230955-75-6(Hazardous Substances Data)

Usage

General Description

6-Quinazolinol,4-chloro-7-methoxy-, 6-acetate, also known as 4-chloro-7-methoxyquinazoline-6-yl acetate, is a chemical compound that is a member of the large quinazoline class of heterocyclic aromatic organic compounds. The molecular formula of this chemical is C11H10ClNO4. Details about its properties such as melting point, boiling point or density are not commonly available, indicating it is probably used or studied in very specific, potentially industrial or pharmaceutical contexts. As with all chemicals, care should be taken to handle it safely and appropriately, in accordance with its material safety data sheet and under the guidance of a professional.

InChI:InChI=1/C11H9ClN2O3/c1-6(15)17-10-3-7-8(4-9(10)16-2)13-5-14-11(7)12/h3-5H,1-2H3

Upstream product

• 7719-09-7 thionyl chloride 
• 179688-53-0 7-methoxy-4-oxo-3,4-dihydroquinazolin-6-yl acetate 
• 179688-52-9 4,6-dihydroxy-7-methoxyquinazoline 
• 4998-07-6 4,5-dimethoxy-2-nitro-benzoic acid 
• 31839-20-0 5-hydroxy-4-methoxy-2-nitrobenzoic acid 
• 31839-21-1 2-amino-5-hydroxy-4-methoxybenzoic acid 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 20357-25-9 6-nitroveratraldehyde 
• 13794-72-4 6,7-dimethoxy-4-hydroxyquinazoline 
• 57535-57-6 methyl 3-(benzyloxy)-4-methoxy-benzoate 
• 6702-50-7 3-hydroxy-4-methoxybenzoate 
• 50413-44-0 methyl 2-amino-5-hydroxy-4-methoxybenzoate 
• 164161-49-3 methyl 5-(benzyloxy)-4-methoxy-2-nitrobenzoate 
• 13790-39-1 6,7-dimethoxy-4-chloroquinazoline 

Downstream Products

• 1439373-52-0 C₂₃H₁₉ClN₄O₄ 
• 451495-03-7 acetic acid 7-ethoxy-4-[3-(3-hydroxy-3-methyl-1-butynyl)phenylamino]-6-quinazolinyl ester 
• 574745-97-4 4-chloro-6-hydroxy-7-methoxyquinazoline 
• 612501-80-1 4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl acetate monohydrochloride 

Relevant articles and documents

Dual nicotinamide phosphoribosyltransferase and epidermal growth factor receptor inhibitors for the treatment of cancer

Multitarget drugs have emerged as a promising treatment modality in modern anticancer therapy. Taking advantage of the synergy of NAMPT and EGFR inhibition, we have developed the first compounds that serve as dual inhibitors of NAMPT and EGFR. On the basis of CHS828 and erlotinib, a series of hybrid molecules were successfully designed and synthesized by merging of the pharmacophores. Among the compounds that were synthesized, compound 28 showed good NAMPT and EGFR inhibition, and excellent in vitro anti-proliferative activity. Compound 28, which is a new chemotype devoid of a Michael receptor, strongly inhibited the proliferation of several cancer cell lines, including H1975 non-small cell lung cancer cells harboring the EGFRL858R/T790M mutation. More importantly, it imparted significant in vivo antitumor efficacy in a human NSCLC (H1975) xenograft nude mouse model. This study provides promising leads for the development of novel antitumor agents and valuable pharmacological probes for the assessment of dual inhibition in NAMPT and EGFR pathway with a single inhibitor.

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.

Compound used as kinase inhibitor, and application thereof

The invention relates to a compound used as a kinase inhibitor, and application thereof. The structure of the compound is shown as a formula I in the specification. The compound used as the kinase inhibitor provided by the invention has good inhibitory activity on EGFR and Her2 exon 20 insertion mutation, and has great potential to be developed into drugs for treating related diseases.