692059-41-9

Usage

Uses

Used in Pharmaceutical Industry:
Gefitinib InterMediate A is used as a key intermediate in the synthesis of Gefitinib, an EGFR inhibitor with significant anti-tumor activity. It contributes to the development of targeted therapies for various types of cancer, including non-small cell lung cancer (NSCLC) and other solid tumors.
Used in Cancer Research:
Gefitinib InterMediate A serves as a valuable compound in cancer research, aiding scientists in understanding the mechanisms of EGFR inhibition and its implications in tumor growth and progression. This knowledge can lead to the discovery of novel therapeutic agents and strategies for cancer treatment.
Used in Drug Development:
As a precursor to Gefitinib, Gefitinib InterMediate A is essential in the drug development process. It helps researchers and pharmaceutical companies optimize the synthesis and formulation of Gefitinib, ensuring its efficacy, safety, and stability as a pharmaceutical product.
Used in Drug Synthesis Education:
Gefitinib InterMediate A can be utilized as a teaching tool in educational settings, particularly in courses related to medicinal chemistry, pharmaceutical sciences, and drug discovery. It provides students with hands-on experience in the synthesis of bioactive compounds and an understanding of the challenges and strategies involved in drug development.

Upstream product

• 574738-93-5 6-(3-chloropropoxy)-7-methoxyquinazolin-4-ol 
• 645-08-9 Isovanillic acid 
• 929683-54-5 3-(3-chloropropoxy)-4-methoxybenzaldehyde 
• 621-59-0 isovanillin 
• 574745-97-4 4-chloro-6-hydroxy-7-methoxyquinazoline 
• 627-30-5 1-chloro-3-hydroxypropane 
• 6702-50-7 3-hydroxy-4-methoxybenzoate 
• 574738-93-5 6-(3-chloropropoxy)-7-methoxyquinazolin-4(3H)-one 
• 380844-24-6 methyl 5-(3-chloropropoxy)-4-methoxy-2-nitrobenzoate 
• 380844-26-8 methyl 5-(3-chloropropoxy)-2-amino-4-methoxybenzoate 
• 380844-22-4 methyl 3-(3-chloropropoxy)-4-methoxybenzoate 

Downstream Products

• 912556-91-3 6-(3-chloropropoxy)-N-(3-chloro-4-fluorophenyl)-7-methoxyquinazolin-4-ylamine 
• 1259017-55-4 3-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-7-methoxyquinazolin-6-yloxy)propyl 4-(bis(4-fluorophenyl)methyl)piperazine-1-carbodithioate 
• 1259017-50-9 3-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-7-methoxyquinazolin-6-yloxy)propyl 4-methylpiperazine-1-carbodithioate 
• 1259017-48-5 3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl 4-methylpiperazine-1-carbodithioate 
• 1259017-46-3 3-(4-(3-bromophenylamino)-7-methoxyquinazolin-6-yloxy)propyl 4-methylpiperazine-1-carbodithioate 
• 1259017-51-0 3-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-7-methoxyquinazolin-6-yloxy)propyl piperazine-1-carbodithioate 
• 1259017-53-2 3-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-7-methoxyquinazolin-6-yloxy)propyl morpholine-4-carbodithioate 
• 1259017-54-3 3-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-7-methoxyquinazolin-6-yloxy)propyl thiomorpholine-4-carbodithioate 
• 1259017-72-5 N-(3-bromophenyl)-6-(3-chloropropoxy)-7-methoxyquinazolin-4-amine 
• 1259017-73-6 N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-(3-chloropropoxy)-7-methoxyquina-zolin-4-amine 
• 1456070-16-8 C₂₃H₂₄ClFN₄O₄S 
• 1456070-17-9 C₂₁H₂₂ClFN₄O₃ 
• 1456070-18-0 C₂₂H₂₄ClFN₄O₃ 
• 1445860-68-3 4-(3'-chloro-4'-fluorophenylamino)-6-[3-(2-oxa-6-azaspiro[3.4]octane-6-yl)propoxy]-7-methoxyquinazoline 

Relevant academic research and scientific papers

Four-membered heterocycles-containing 4-anilino-quinazoline derivatives as epidermal growth factor receptor (EGFR) kinase inhibitors

We report herein the design and synthesis of novel azaspirocycle or azetidine substituted 4-anilinoquinazoline derivatives. The EGFR inhibitory activities and in vitro antitumor potency of these newly synthesized compounds against two lung cancer cell lines HCC827 and A549 were evaluated. Most of the target compounds possess good inhibitory potency. In particular, compounds 21g with 2-oxa-6-azaspiro[3.4]octane substituent was found to possess higher EGFR inhibitory activities and similar antitumor potency comparing to the lead compound gefitinib with improved water solubility.

Novel EGFR inhibitors prepared by combination of dithiocarbamic acid esters and 4-anilinoquinazolines

On the basis of combination strategy, a novel series of EGFR inhibitors were designed and synthesized by combination of dithiocarbamic acid esters and 4-anilinoquinazolines. The effect of the synthesized compounds on cell proliferation was evaluated by MTT assay in three human cancer cell lines: MDA-MB-468, SK-BR-3 and HCT-116. Two compounds (11d and 11f) were found more potent against all three cell lines and five compounds (11a, 11d-11g) were found more potent against both MDA-MB-468 and SK-BR-3 than Lapatinib. SAR studies revealed that the substituents on C6 and C7 positions of quinazoline, the amine component of dithiocarbamate moiety and the linker greatly affected the activity. This work provides a promising new strategy for the preparation of potent tyrosine kinase inhibitors.

4-Quinazolinyloxy-diaryl ureas as novel BRAFV600E inhibitors

Aryl phenyl ureas with a 4-quinazolinoxy substituent at the meta-position of the phenyl ring are potent inhibitors of mutant and wild type BRAF kinase. Compound 7 (1-(5-tert-butylisoxazol-3-yl)-3-(3-(6,7-dimethoxyquinazolin-4-yloxy) phenyl)urea hydrochloride) exhibits good pharmacokinetic properties in rat and mouse and is efficacious in a mouse tumor xenograft model following oral dosing.

Design, synthesis, and in vitro antitumor activity evaluation of novel 4-pyrrylamino quinazoline derivatives

Here, we describe the design and synthesis of two series of 4-pyrrylamino quinazolines as new analogs of the epidermal growth factor receptor inhibitor gefitinib. In vitro antitumor activity of these novel compounds against pancreatic (Miapaca2) and prostate (DU145) cancer cell lines was evaluated. Compared with the parental gefitinib, all 18 derivatives show a greatly increased cytotoxicity to cancer cells. In vitro kinase inhibitory activity on epidermal growth factor receptor was also investigated. Among them, compounds GI-6, GII-4, GII-6, GII-8, and GII-9 are more potential receptor tyrosine kinase (RTK) inhibitors. Based on these results, we propose simple structure-activity relationship to provide information for designing and developing more potent antitumor agents.

Design, synthesis of novel quinazolone alkaloids derivatives as potential antitumor agents

Several novel quinazolone alkaloids derivatives were synthesized. Some of the target compounds were determined against human prostate cancer DU145 and pancreatic cancer Miacapa2 cells in vitro. The entire compounds had been identified by 1HNMR, 13CNMR, IR, MS and EA.

Design and synthesis of novel Gefitinib analogues with improved anti-tumor activity

There is an urgent need to design and develop new and more potent EGFR inhibitors with improved anti-tumor activity. Here we describe the design and synthesis of two series of 4-benzothienyl amino quinazolines as new analogues of the EGFR inhibitor Gefiti

Design, synthesis, docking and antitumor activity of quinazolino [3, 4-a] thieno [3, 2-d] pyrimidin-8-one derivatives

Several novel quinazolino [3, 4-a] thieno [3, 2-d] pyrimidin-8-one derivatives were synthesized. All of the compounds were determined against MiaPaCa2 and DU145 cells in vitro, and the crystal structures of analog 8 and 20 in the active site of the EGFR c

QUINAZOLINE DERIVATIVES AS RAF KINASE MODULATORS AND METHODS OF USE THEREOF

Compounds according to formula (I), compositions and methods are provided for modulating the activity of RAF kinases, including BRAF kinase and for the treatment, prevention, or amelioration of one or more symptoms of disease or disorder mediated by RAF kinases. Formula (I): or a pharmaceutically acceptable salt, solvate, clathrate of hydrate thereof, wherein X is O or S(O)t; Ra is O or S.

PROCESS FOR THE PREPARATION OF GEFITINIB

There is provided a compound of formula (III), and a process for preparing a compound of formula (V) comprising converting a compound of formula (III) to the compound (V), wherein (X) is fluoro, chloro, bromo or iodo. There is also provided a process for preparing a compound of formula (Xl) comprising converting a compound of formula (X) to the compound (Xl). The compounds (V) and (Xl) so prepared may be used in a process for preparing gefitinib.

Synthesis of gefitinib from methyl 3-hydroxy-4-methoxy-benzoate

This paper reports a novel synthesis of gefitinib starting from methyl 3-hydroxy-4-methoxybenzoate. The process starts with alkylation of the starting material, followed by nitration, reduction, cyclization, chlorination and two successive amination reactions. The intermediates and target molecule were characterized by 1H-NMR, 13C-NMR, MS and the purities of all these compounds were determined by HPLC. This novel synthetic route produced overall yields as high as 37.4%.