164161-49-3

Usage

Uses

Used in Organic Synthesis:
Methyl 5-Benzyloxy-4-Methoxy-2-nitrobenzoate is utilized as a building block in the production of various pharmaceuticals and agrochemicals. Its structural features allow it to serve as a versatile intermediate in the synthesis of a wide range of organic compounds, particularly those with potential therapeutic or pesticidal properties.
Used in Photopolymerization Reactions:
Methyl 5-Benzyloxy-4-Methoxy-2-nitrobenzoate is recognized for its potential use as a photoinitiator in photopolymerization processes. Its ability to absorb light and generate reactive species upon exposure makes it a valuable component in the formulation of materials that cure under UV or visible light, facilitating rapid and efficient polymerization reactions in various industrial applications.

Upstream product

• 57535-57-6 methyl 3-(benzyloxy)-4-methoxy-benzoate 
• 6702-50-7 3-hydroxy-4-methoxybenzoate 
• 100-39-0 benzyl bromide 
• 621-59-0 isovanillin 
• 645-08-9 Isovanillic acid 
• 215659-03-3 methyl 5-hydroxy-4-methoxy-2-nitrobenzoate 
• 4998-07-6 4,5-dimethoxy-2-nitro-benzoic acid 
• 31839-20-0 5-hydroxy-4-methoxy-2-nitrobenzoic acid 

Downstream Products

• 909912-09-0 benzyl 2-amino-5-(benzyloxy)-4-methoxybenzoic acid 
• 1006890-01-2 7-methoxy-4-pyridin-3-yl-6-(2-quinolin-2-ylethoxy)quinazoline 
• 1311509-51-9 6-(benzyloxy)-7-methoxy-3-methylquinazolin-4(3H)-one 
• 1006890-13-6 6-(benzyloxy)-7-methoxy-N,N-dimethylquinazolin-4-amine 
• 1006889-93-5 6-(benzyloxy)-7-methoxy-4-(pyridin-3-yl)quinazoline 
• 286371-64-0 6-(benzyloxy)-7-methoxyquinazolin-4(3H)-one 
• 1188908-25-9 1-(5-tert-butylisoxazol-3-yl)-3-(3-(6-hydroxy-7-methoxyquinazolin-4-yloxy)phenyl)urea 
• 286371-64-0 C₁₆H₁₄N₂O₃ 
• 1188908-26-0 C₂₂H₁₉N₃O₃ 
• 1188908-27-1 4-(3-aminophenoxy)-7-methoxyquinazolin-6-ol 
• 184475-35-2 gefitinib 
• 913819-12-2 6-(benzyloxy)-N-(3-chloro-4-fluorophenyl)-7-methoxyquinazolin-4-amine 
• 184475-71-6 4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline 
• 179688-53-0 6-acetoxy-7-methoxy-3,4-dihydroquinazolin-4-one 

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.

Synthesis, biological evaluation and molecular docking studies of novel 1,2,3-triazole-quinazolines as antiproliferative agents displaying ERK inhibitory activity

ERK1/2 inhibitors have attracted special attention concerning the ability of circumventing cases of innate or log-term acquired resistance to RAF and MEK kinase inhibitors. Based on the 4-aminoquinazoline pharmacophore of kinases, herein we describe the synthesis of 4-aminoquinazoline derivatives bearing a 1,2,3-triazole stable core to bridge different aromatic and heterocyclic rings using copper-catalysed azide-alkyne cycloaddition reaction (CuAAC) as a Click Chemistry strategy. The initial screening of twelve derivatives in tumoral cells (CAL-27, HN13, HGC-27, and BT-20) revealed that the most active in BT-20 cells (25a, IC50 24.6 μM and a SI of 3.25) contains a more polar side chain (sulfone). Furthermore, compound 25a promoted a significant release of lactate dehydrogenase (LDH), suggesting the induction of cell death by necrosis. In addition, this compound induced G0/G1 stalling in BT-20 cells, which was accompanied by a decrease in the S phase. Western blot analysis of the levels of p-STAT3, p-ERK, PARP, p53 and cleaved caspase-3 revealed p-ERK1/2 and p-STA3 were drastically decreased in BT-20 cells under 25a incubation, suggesting the involvement of these two kinases in the mechanisms underlying 25a-induced cell cycle arrest, besides loss of proliferation and viability of the breast cancer cell. Molecular docking simulations using the ERK-ulixertinib crystallographic complex showed compound 25a could potentially compete with ATP for binding to ERK in a slightly higher affinity than the reference ERK1/2 inhibitor. Further in silico analyses showed comparable toxicity and pharmacokinetic profiles for compound 25a in relation to ulixertinib.

QUINAZOLINONE COMPOUNDS

New quinazolinone compounds are disclosed, as well as pharmaceutical compositions containing quinazolinones and methods for the treatment of diseases and conditions associated with mitochondrial dysfunction.

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

HETEROCYCLIC INHIBITORS OF TYROSINE KINASE

The present disclosure relates to heterocyclic compounds and methods which may be useful as inhibitors of HER2 or EGFR for the treatment or prevention of disease, including cancer.

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.

Substituted 2-arylbenzothiazoles as kinase inhibitors: Hit-to-lead optimization

Based on an (aminoaryl)benzothiazole quinazoline hit structure for kinase inhibition, a systematic optimization program resulted in a lead structure allowing for inhibitory activities in cellular phosphorylation assays in the low nanomolar range.

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.