913819-12-2

Basic information

• Product Name: N-(3-Chloro-4-fluorophenyl)-7-methoxy-6-(phenylmethoxy)-4-quinazolinamine
• Synonyms: N-(3-Chloro-4-fluorophenyl)-7-methoxy-6-(phenylmethoxy)-4-quinazolinamine
• CAS NO: 913819-12-2
• Molecular Formula: C₂₂H₁₇ClFN₃O₂
• Molecular Weight: 409.846
• Mol File: 913819-12-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Density: 1.362
• CAS DataBase Reference: N-(3-Chloro-4-fluorophenyl)-7-methoxy-6-(phenylmethoxy)-4-quinazolinamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-Chloro-4-fluorophenyl)-7-methoxy-6-(phenylmethoxy)-4-quinazolinamine(913819-12-2)
• EPA Substance Registry System: N-(3-Chloro-4-fluorophenyl)-7-methoxy-6-(phenylmethoxy)-4-quinazolinamine(913819-12-2)

Safety Data

• Hazardous Substances Data: 913819-12-2(Hazardous Substances Data)

Usage

General Description

The chemical N-(3-Chloro-4-fluorophenyl)-7-methoxy-6-(phenylmethoxy)-4-quinazolinamine is a quinazolinamine derivative with a substituted phenyl group containing both chlorine and fluorine atoms, as well as a methoxy group. It also contains a phenylmethoxy group. N-(3-Chloro-4-fluorophenyl)-7-methoxy-6-(phenylmethoxy)-4-quinazolinamine has potential pharmaceutical applications due to its interesting molecular structure and the presence of functional groups that can interact with biological targets. Further research and investigation into its biological and pharmacological properties could reveal its potential as a drug candidate for various therapeutic purposes.

Upstream product

• 367-21-5 3-chloro-4-fluorophenylamine 
• 286371-65-1 6-(benzyloxy)-4-chloro-7-methoxyquinazoline 
• 621-59-0 isovanillin 
• 645-08-9 Isovanillic acid 
• 6702-50-7 3-hydroxy-4-methoxybenzoate 
• 57535-57-6 methyl 3-(benzyloxy)-4-methoxy-benzoate 
• 164161-49-3 methyl 5-(benzyloxy)-4-methoxy-2-nitrobenzoate 
• 855793-63-4 methyl 2-amino-5-(benzyloxy)-4-methoxybenzoate 
• 286371-64-0 6-(benzyloxy)-7-methoxyquinazolin-4(3H)-one 
• 52805-46-6 2-methoxy-5-cyanophenol 
• 52805-37-5 3-benzyloxy-4-methoxybenzonitrile 
• 192869-56-0 5-benzyloxy-4-methoxy-2-nitro-benzonitrile 
• 192869-57-1 2-amino-5-benzyloxy-4-methoxybenzonitrile 
• 100-39-0 benzyl bromide 

Downstream Products

• 184475-71-6 4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline 

Relevant articles and documents

Novel amide analogues of quinazoline carboxylate display selective antiproliferative activity and potent EGFR inhibition

In the present study, a novel series of quinazoline derivatives is developed for cancer therapy. All the synthesised analogues were evaluated against a panel of 60 human cancer cell lines for the antiproliferative activity. Significant and selective growth inhibition of several solid tumour cell lines such as NCI-H322M, NCI-H522 (non-small cell lung cancer), IGROV1, SK-OV-3 (ovarian cancer), TK-10 (renal cancer) and MDA-MB-468 (breast cancer) was observed. Further, all the new amide analogues strongly inhibited EGFR in low nanomolar range with morpholino quinazoline 10 producing activity (IC50 = 6.12 nM) comparable to standard drugs erlotinib and gefitinib. In addition, western blot analysis depicted inhibition of phosphorylation of EGFR by compounds 10 and 11 in MDA-MB-468 cells at 10 μM. Molecular docking studies showed the strong binding interactions with the active site of the EGFR protein. The current investigation could be extremely helpful for the development of newer therapeutically useful quinazoline based molecules for cancer therapy.

Optimization of gefitinib analogues with potent anticancer activity

The interactions of gefitinib (Iressa) in EGFR are hydrogen bonding and van der Waals forces through quinazoline and aniline rings. However the morpholino group of gefitinib is poorly ordered due to its weak electron density. A series of novel piperazino analogues of gefitinib where morpholino group substituted with various piperazino groups were designed and synthesized. Most of them indicated significant anti-cancer activities against human cancer cell lines. In particular, compounds 52-54 showed excellent potency against cancer cells. Convergent synthetic approach has been developed for the synthesis of gefitinib intermediate which can lead to gefitinib as well as numerous analogues.

Spiro compounds and methods of use

The present invention relates to spiro compounds of formula I, processes for their preparation, pharmaceutical compositions containing them as active ingredient, methods for the treatment of disease states such as cancers associated with protein tyrosine kinases, especially epidermal growth factor (EGF) and vascular endothelial growth factor (VEGF), to their method of use as medicaments and to their method of use in the manufacture of medicaments for use in the production of inhibition of tyrosine kinase reducing effects in warm-blooded animals such as humans.