230955-75-6

Usage

Uses

6-Quinazolinol,4-chloro-7-methoxy-, 6-acetate is used in various applications across different industries, primarily due to its unique chemical structure and properties. Some of the key applications include:
1. Pharmaceutical Industry:
6-Quinazolinol,4-chloro-7-methoxy-, 6-acetate is used as a pharmaceutical intermediate for the synthesis of various therapeutic agents. Its unique structure allows it to be a key component in the development of drugs targeting specific biological pathways or receptors, potentially leading to the creation of novel treatments for various diseases.
2. Chemical Research:
In the field of chemical research, 6-Quinazolinol,4-chloro-7-methoxy-, 6-acetate serves as a valuable compound for studying the properties and reactivity of quinazoline derivatives. Its synthesis and modification can provide insights into the development of new synthetic routes and the exploration of its potential applications in various chemical processes.
3. Material Science:
6-Quinazolinol,4-chloro-7-methoxy-, 6-acetate may also find use in material science, particularly in the development of new materials with specific properties. Its incorporation into polymers or other materials could potentially enhance their performance or introduce new functionalities, such as improved stability, conductivity, or catalytic activity.
4. Agrochemical Industry:
In the agrochemical sector, 6-Quinazolinol,4-chloro-7-methoxy-, 6-acetate could be utilized as a precursor for the synthesis of bioactive compounds with potential applications in pest control, crop protection, or as growth regulators. Its unique structure may contribute to the development of novel agrochemicals with improved efficacy and selectivity.
5. Dye and Pigment Industry:
6-Quinazolinol,4-chloro-7-methoxy-, 6-acetate, due to its aromatic nature, may be employed in the dye and pigment industry for the development of new colorants with specific properties. Its incorporation into dye molecules could lead to the creation of dyes with improved colorfastness, brightness, or stability.

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

• 108-24-7 acetic anhydride 
• 179688-52-9 6-hydroxy-7-methoxyquinazolin-4(3H)-one 
• 179688-53-0 7-methoxy-4-oxo-3,4-dihydroquinazolin-6-yl acetate 
• 7719-09-7 thionyl chloride 
• 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 
• 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 
• 26791-93-5 methyl 4,5-dimethoxy-2-nitrobenzoate 
• 199327-61-2 7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one 
• 13790-39-1 6,7-dimethoxy-4-chloroquinazoline 

Downstream Products

• 788136-89-0 4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl acetate 
• 687995-79-5 acetic acid 7-methoxy-4-{2-methyl-5-[(2-morpholin-4-yl-pyridine-4-carbonyl)-amino]-phenylamino}-quinazolin-6-yl ester 
• 740081-22-5 4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl acetate 
• 1012057-17-8 4-(3-ethynylphenylamino)-7-methoxyquinazolin-6-yl acetate hydrochloride 
• 320366-67-4 N-diphenylmethylene-6-acetoxy-7-methoxyquinazolin-4-amine 
• 1439373-52-0 C₂₃H₁₉ClN₄O₄ 
• 451495-03-7 acetic acid 7-ethoxy-4-[3-(3-hydroxy-3-methyl-1-butynyl)phenylamino]-6-quinazolinyl ester 
• 697299-93-7 4-[3-Chloro-4-(pyridin-2-ylmethoxy)-phenylamino]-7-methoxy-quinazolin-6-ol 
• 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 academic research and scientific papers

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.

IMINO SULFANONE INHIBITORS OF ENPP1

The present disclosure relates generally to inhibitors of ectonucleotide pyrophosphatase/phosphodiesterase 1 (ENPP1), compositions thereof, and methods of using said compounds and compositions thereof. More specifically, the present disclosure relates to sulfoximine- based inhibitors of ENPP1 of Formula (I) and methods of their use for treating disease mediated by ENPP1.

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.

Synthesis, crystal structure and anticancer activity of substituted quinazoline derivatives

News series of substituted quinazoline derivatives has been synthesized from 3,4-dihydro-7-methoxy-4-oxoquinazoline-6-yl acetate (1) by five-step procedures including chlorination, amination, hydrolysis and etherification. The structures of target compounds were confirmed by IR, 1H-NMR, element analysis and single-crystal X-ray diffraction. The results showed that the compound 8c exhibited remarkable inhibitory activity against MCF-7 cell lines with inhibition rate value of 38.45 %, which was comparable to that of the positive control Gefitinib (inhibition rate = 13.25 % for MCF-7). The initial relationship between structure and activity was worth further exploration.

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.

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).

COMPOSITIONS AND METHODS FOR TREATING CANCER

The present disclosure relates to compounds that are capable penetrating to the blood brain barrier to modulate the activity of EGFR tyrosine kinase. The disclosure further relates to methods of treating Glioblastoma and other EGFR mediated cancers. The disclosure further relates to methods of treating Glioblastoma and other EGFR mediated cancers that have been determined to have altered glucose metabolism in the presence of inhibitors. The present disclosure also provides methods of administering to a subject a glucose metabolism inhibitor and a cytoplasmic p53 stabilizer.

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 tyrosine kinase inhibitor AZD3759

The invention provides a preparation method of a tyrosine kinase inhibitor AZD3759, and relates to the field of medicinal chemistry. The preparation method comprises the following steps: by taking 3,4-dihydro-7-methoxy-4-oxoquinazoline-6-alcohol acetate as a raw material, carrying out a chlorination reaction and a hydrolysis reaction to obtain 4-chloro-7-methoxyquinazoline-6-alcohol (a compound 3); taking (R)-(-)-2-methylpiperazine as a raw material, and obtaining (R)-4-chlorocarbonyl-3-tert-butyl formate (compound 6) through a nucleophilic addition-elimination reaction and a chloroformylation reaction; carrying out an esterification reaction on the compound 3 and the compound 6 to obtain a compound 7; carrying out a Boc removal reaction and a methylation reaction on the compound 7 to obtain a compound 9; and carrying out alkylation reaction on the compound 9 and 2-fluoro-3-chloroaniline to obtain AZD3759. The method has the advantages of cheap and accessible raw materials and lower cost; sodium cyanoborohydride is not used in the reaction process, so that the method is more environment-friendly and is beneficial to industrial large-scale production.

Hetero-aromatic compound and its use in medicine

The invention provides a hetero-aromatic compound or a stereisomer, geometric isomer, tautomer, despinner, nitrogen oxide, hydrate, solvate, metabolite, metabolism precursor and pharmaceutically acceptable salt or prodrug thereof, which is used for treating proliferative diseases. The invention also discloses a pharmaceutical composition containing the compound and an application of the compound or pharmaceutical composition thereof in preparation of a medicine for treating proliferative diseases.