286371-65-1

Usage

Uses

Used in Pharmaceutical Research and Development:
4-Chloro-7-methoxy-6-benzyloxyquinazoline is utilized as a building block in the synthesis of various biologically active molecules. It serves as a key intermediate in the creation of potential anticancer and antimalarial drugs, contributing to the advancement of novel therapeutic agents.
Used in Anticancer Drug Development:
In the field of oncology, 4-Chloro-7-methoxy-6-benzyloxyquinazoline is used as a precursor for developing new anticancer agents. Its unique structure allows for the design of molecules that can target and combat cancer cells, offering a promising avenue for cancer treatment.
Used in Antimalarial Drug Development:
Similarly, 4-Chloro-7-methoxy-6-benzyloxyquinazoline is employed in the development of antimalarial drugs, where its structural properties can be leveraged to create effective treatments against malaria, a disease affecting millions worldwide.
Used in Antifungal and Antibacterial Applications:
4-Chloro-7-methoxy-6-benzyloxyquinazoline has also been studied for its potential as an antifungal and antibacterial agent. Its application in these areas highlights its versatility in medicinal chemistry, where it can be used to combat a range of infectious diseases.
Used in Medicinal Chemistry Research:
In research laboratories, 4-Chloro-7-methoxy-6-benzyloxyquinazoline is used to explore its chemical properties and potential interactions with biological systems. This research is crucial for understanding its mechanisms of action and optimizing its use in drug development.

InChI:InChI=1/C16H13ClN2O2/c1-20-14-8-13-12(16(17)19-10-18-13)7-15(14)21-9-11-5-3-2-4-6-11/h2-8,10H,9H2,1H3

Upstream product

• 215659-03-3 methyl 5-hydroxy-4-methoxy-2-nitrobenzoate 
• 909912-09-0 benzyl 2-amino-5-(benzyloxy)-4-methoxybenzoic acid 
• 31839-20-0 5-hydroxy-4-methoxy-2-nitrobenzoic acid 
• 4998-07-6 4,5-dimethoxy-2-nitro-benzoic acid 
• 26791-93-5 methyl 4,5-dimethoxy-2-nitrobenzoate 
• 621-59-0 isovanillin 
• 6702-50-7 3-hydroxy-4-methoxybenzoate 
• 57535-57-6 methyl 3-(benzyloxy)-4-methoxy-benzoate 
• 100-39-0 benzyl bromide 
• 230955-75-6 6-acetoxy-4-chloro-7-methoxyquinazoline 
• 574745-97-4 4-chloro-6-hydroxy-7-methoxyquinazoline 
• 286371-64-0 C₁₆H₁₄N₂O₃ 
• 634197-80-1 2-amino-5-benzyloxy-4-methoxybenzoic acid benzyl ester 
• 634198-01-9 5-benzyloxy-4-methoxy-2-nitrobenzoic acid benzyl ester 

Downstream Products

• 205259-46-7 4-(6-benzyloxy-7-methoxy-4-quinazolinyl)-1-piperazinecarboxylic acid tert-butyl ester 
• 1006889-92-4 6-(benzyloxy)-7-methoxy-4-phenylquinazoline 
• 1006890-12-5 6-(benzyloxy)-7-methoxy-4-morpholinoquinazoline 
• 913819-12-2 6-(benzyloxy)-N-(3-chloro-4-fluorophenyl)-7-methoxyquinazolin-4-amine 
• 1006890-13-6 6-(benzyloxy)-7-methoxy-N,N-dimethylquinazolin-4-amine 
• 1006889-93-5 6-(benzyloxy)-7-methoxy-4-(pyridin-3-yl)quinazoline 
• 1006890-01-2 7-methoxy-4-pyridin-3-yl-6-(2-quinolin-2-ylethoxy)quinazoline 
• 1638151-52-6 (R)-2-((7-methoxy-4-(3-(quinoxaline-2-yloxy)-pyrrolidine-1-yl)-quinazoline-6-yl)-oxy)ethyl 4-methylbenzenesulphonate 
• 184475-35-2 gefitinib 
• 184475-71-6 4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline 
• 1188908-27-1 4-(3-aminophenoxy)-7-methoxyquinazolin-6-ol 
• 1188908-25-9 1-(5-tert-butylisoxazol-3-yl)-3-(3-(6-hydroxy-7-methoxyquinazolin-4-yloxy)phenyl)urea 
• 634197-88-9 4-(6-benzyloxy-7-methoxy-quinazolin-4-yl)-piperazine-1-carboxylic acid (4-cyano-phenyl)-amide 

Relevant academic research and scientific papers

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.

Structure–activity relationship study of novel quinazoline-based 1,6-naphthyridinones as MET inhibitors with potent antitumor efficacy

As a privileged scaffold, the quinazoline ring is widely used in the development of EGFR inhibitors, while few quinazoline-based MET inhibitors are reported. In our ongoing efforts to develop new MET-targeted anticancer drug candidates, a series of quinaz

Absolute Binding Free Energy Calculation and Design of a Subnanomolar Inhibitor of Phosphodiesterase-10

Accurate prediction of absolute protein-ligand binding free energy could considerably enhance the success rate of structure-based drug design but is extremely challenging and time-consuming. Free energy perturbation (FEP) has been proven reliable but is limited to prediction of relative binding free energies of similar ligands (with only minor structural differences) in binding with a same drug target in practical drug design applications. Herein, a Gaussian algorithm-enhanced FEP (GA-FEP) protocol has been developed to enhance the FEP simulation performance, enabling to efficiently carry out the FEP simulations on vanishing the whole ligand and, thus, predict the absolute binding free energies (ABFEs). Using the GA-FEP protocol, the FEP simulations for the ABFE calculation (denoted as GA-FEP/ABFE) can achieve a satisfactory accuracy for both structurally similar and diverse ligands in a dataset of more than 100 receptor-ligand systems. Further, our GA-FEP/ABFE-guided lead optimization against phosphodiesterase-10 led to the discovery of a subnanomolar inhibitor (IC50 = 0.87 nM, ~2000-fold improvement in potency) with cocrystal confirmation.

A class of methods for quinoline compound and its preparation method and application (by machine translation)

The invention discloses a quinazolinone quinoline compound and its preparation method and application, the states kuikui zuo lin the apperception compound of formula (I) has a structure shown in, wherein R is a cyclic or non-cyclic aliphatic amine, aromatic or heterocyclic amine, acyl-containing groups, containing a hydroxy group, mercapto-containing group; R1 For hydrogen or methoxy, methyl, ethyl, halogen, trifluoromethyl, ethoxy, acetyl, cyano, nitro, N, N - dimethyl, methyl, benzyloxy, non-substituted or substituted amino, substituted guanidino, substituted or non-substituted phosphate group, substituted or non-substituted sulfonic acid group, heterocyclic substituted the end is fragrant or the end of a long chain aliphatic alkane groups and bases. The invention provides a quinazoline compound is a kind of structure of novel compound, and the compound to phosphodiesterase 10 type good inhibition effect, while at the same time to phosphodiesterase 3 type has an excellent selectivity, can be used as a phosphodiesterase 10 type of selective inhibitor. In addition, the quinazoline compounds of the invention of the preparation method with quick, simple, low cost and the like. (by machine translation)

Fluorine-containing 6,7-dialkoxybiaryl-based inhibitors for phosphodiesterase 10 A: Synthesis and in vitro evaluation of inhibitory potency, selectivity, and metabolism

Based on the potent phosphodiesterase 10 A (PDE10A) inhibitor PQ-10, we synthesized 32 derivatives to determine relationships between their molecular structure and binding properties. Their roles as potential positron emission tomography (PET) ligands were evaluated, as well as their inhibitory potency toward PDE10A and other PDEs, and their metabolic stability was determined in vitro. According to our findings, halo-alkyl substituents at position 2 of the quinazoline moiety and/or halo-alkyloxy substituents at positions 6 or 7 affect not only the compounds′ affinity, but also their selectivity toward PDE10A. As a result of substituting the methoxy group for a monofluoroethoxy or difluoroethoxy group at position 6 of the quinazoline ring, the selectivity for PDE10A over PDE3A increased. The same result was obtained by 6,7-difluoride substitution on the quinoxaline moiety. Finally, fluorinated compounds (R)-7-(fluoromethoxy)-6-methoxy-4-(3-(quinoxaline-2-yloxy)pyrrolidine-1-yl) quinazoline (16 a), 19 a-d, (R)-tert-butyl-3-(6-fluoroquinoxalin-2-yloxy) pyrrolidine-1-carboxylate (29), and 35 (IC50 PDE10A 11-65 nM) showed the highest inhibitory potential. Further, fluoroethoxy substitution at position 7 of the quinazoline ring improved metabolic stability over that of the lead structure PQ-10. Fluor your health: Phosphodiesterase 10 A (PDE10A) has emerged as an attractive target for the development of 18F-labelled brain imaging agents for positron emission tomography. A series of fluorinated dialkoxybiaryl compounds were synthesized and evaluated as PDE10A inhibitors, assisted by QSAR docking studies. The 7-fluoromethoxy derivative appears to be a promising candidate for further development.

A simple and highly efficient process for synthesis of Gefitinib and its intermediate

A highly efficient one pot conversion of 4-methoxy-3-benzyloxy-6-nitro benzoate to 6-benzoyloxy-7-methoxy quinazoline-4-one using Fe/acetic acid and formamidine acetate followed by debenzylation of 4-(3-chloro-4-flurophenylamino)-6-benzoyloxy-7-methoxy quinazoline using methanesulfonic acid in chloroform is described. Additionally the desmethyl impurity formation is controlled using oxalyl chloride and DIPEA.

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.

Use of structure-based design to discover a potent, selective, in vivo active phosphodiesterase 10A inhibitor lead series for the treatment of schizophrenia

Utilizing structure-based virtual library design and scoring, a novel chimeric series of phosphodiesterase 10A (PDE10A) inhibitors was discovered by synergizing binding site interactions and ADME properties of two chemotypes. Virtual libraries were docked and scored for potential binding ability, followed by visual inspection to prioritize analogs for parallel and directed synthesis. The process yielded highly potent and selective compounds such as 16. New X-ray cocrystal structures enabled rational design of substituents that resulted in the successful optimization of physical properties to produce in vivo activity and to modulate microsomal clearance and permeability.

HETEROAROMATIC QUINOLINE-BASED COMPOUNDS

The invention pertains to heteroaromatic compounds that serve as effective phosphodiesterase (PDE) inhibitors. The invention also relates to compounds which are selective inhibitors of PDE10. The invention further relates to intermediates for preparation of such compounds; pharmaceutical compositions comprising such compounds; and the use of such compounds in methods for treating certain central nervous system (CNS) or other disorders. The invention relates also to methods for treating neurodegenerative and psychiatric disorders, for example psychosis and disorders comprising deficient cognition as a symptom.

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.