35241-23-7

Usage

Uses

Used in Pharmaceutical Industry:
6,7-DIMETHOXY-2-METHYLQUINAZOLIN-4-OL is used as a potential drug candidate for its anti-inflammatory properties, offering a new avenue for the treatment of inflammatory conditions by modulating the immune response and reducing inflammation.
Used in Anticancer Applications:
In the field of oncology, 6,7-DIMETHOXY-2-METHYLQUINAZOLIN-4-OL is utilized as an anticancer agent, targeting various types of cancer by interfering with cellular processes that promote tumor growth and survival. Its potential to act against multiple cancer types makes it a valuable asset in the development of novel cancer therapies.
Used in Antimicrobial Applications:
6,7-DIMETHOXY-2-METHYLQUINAZOLIN-4-OL is employed as an antimicrobial agent, leveraging its ability to combat microbial infections by inhibiting the growth of bacteria, fungi, or other pathogens, thereby contributing to the development of new antimicrobial drugs.
Used in Research and Development:
In the scientific research domain, 6,7-DIMETHOXY-2-METHYLQUINAZOLIN-4-OL serves as a valuable compound for studying its pharmacological effects and mechanisms of action. This research is crucial for understanding its potential applications and optimizing its use in therapeutic interventions.
Used in Alzheimer's Disease Research:
6,7-DIMETHOXY-2-METHYLQUINAZOLIN-4-OL is used as a potential therapeutic agent in Alzheimer's disease research, exploring its capacity to address the complex pathology of the condition, including its effects on neuroinflammation and amyloid-beta aggregation, which are hallmarks of Alzheimer's disease.
Overall, the diverse applications of 6,7-DIMETHOXY-2-METHYLQUINAZOLIN-4-OL across various medical and scientific fields underscore its potential as a versatile and promising compound for future pharmaceutical development.

InChI:InChI=1/C11H12N2O3/c1-6-12-8-5-10(16-3)9(15-2)4-7(8)11(14)13-6/h4-5H,1-3H3,(H,12,13,14)

Upstream product

• 6286-65-3 6,7-dimethoxy-2-methyl-4H-benzo[d] [1,3]oxazin-4-one 
• 92340-02-8 C₂₂H₂₂N₄O₄S₂ 
• 66299-70-5 6,7-dimethoxy-2-methylquinazoline-4(3H)-thione 
• 26759-46-6 methyl 2-amino-4,5-dimethoxybenzoate 
• 75-05-8 acetonitrile 
• 145352-75-6 2-acetamido-4,5-dimethoxybenzoic acid 
• 20323-74-4 2-carboethoxy-4,5-dimethoxyaniline 
• 61203-48-3 2-iodo-4,5-dimethoxybenzoic acid 
• 124-42-5 acetamidine hydrochloride 
• 6286-46-0 2-bromo-4,5-dimethoxybenzoic acid 
• 631-61-8 ammonium acetate 
• 63190-57-8 methyl 2-acetamido-4,5-diemthoxy benzoate 
• 924301-64-4 4,5-dimethoxy-2-(3-methylfuroxan-4-yl)phenylamine 
• 5653-40-7 2-Amino-4,5-dimethoxybenzoic acid 

Downstream Products

• 50377-49-6 4-chloro-6,7-dimethoxy-2-methylquinazoline 
• 127033-39-0 6,7-Dimethoxy-2-((E)-styryl)-3H-quinazolin-4-one 

Relevant academic research and scientific papers

Design, synthesis and anticancer evaluation of structurally modified substituted aryl-quinazoline derivatives as anticancer agents

A new library of structurally modified aryl quinazoline-isoxazole (12a–j) derivatives have been designed, synthesized and characterized by 1HNMR, 13CNMR and mass spectral data. Further these compounds were evaluated for anticancer applications against four human cancer cell lines including PC3, DU-145 (prostate cancer), A549 (lung cancer) and MCF-7 (breast cancer) by utilizing the MTT assay. The results were compared with etoposide which was used as positive control. Most of the compounds showed good to moderate anticancer activities against the four cancer cell lines. Among them, compounds 12a, 12b, 12c, 12d and 12j exhibited more potent activities. Further, molecular docking studies were carried out for all synthesized compounds against the cancer targets Selective Human Androgen Receptor (PDB ID: 3V49) and Abl-Tyrosine kinase (PDB ID: 1IEP). All the docked ligands have exhibited good binding interactions with the targeted protein.

Synthesis and Transformation of 4-(1-Chloro-1-nitroethyl)-6,7-dimethoxy-2-methylquinazoline: Spectral Characterization and Anti-cancer Properties of some Novel Quinazoline Derivatives

An efficient and simple method has been reported for the synthesis of 4-(1-Chloro-1-nitroethyl)-6,7-dimethoxy-2-methylquinazoline (2) as a key compound for further transformation to other novel 6,7-dimethoxy-2-methyl-4-substituted quinazolines. The structure of the synthesized compounds was characterized by spectroscopic methods. The pathway of some unprecedented reactions was proposed. (E)-1-(6,7-dimethoxy-2-methylquinazolin-4-yl)-3-(4-nitrophenyl)prop-2-en-1-one (11) exhibits high in vitro cytotoxicity on three cell lines, Hepatocellular carcinoma (Hep-G2), Human lung carcinoma (LU-1), and Human breast carcinoma (MCF-7) with IC50 of 2.1, 11.6 and 2.2 μM, respectively.

Cobalt-Catalyzed Tandem Transformation of 2-Aminobenzonitriles to Quinazolinones Using Hydration and Dehydrogenative Coupling Strategy

A tandem synthesis of quinazolinones from 2-aminobenzonitriles is demonstrated here by using an aliphatic alcohol-water system. For this transformation, a cheap and easily available cobalt salt and P(CH2CH2PPh2)3 (PP3) ligand were employed. The substrate scope, scalability, and synthesis of natural products exhibited the vitality of this protocol.

Discovery and development of extreme selective inhibitors of the ITD and D835Y mutant FLT3 kinases

Aberrant activation of FMS-like tyrosine receptor kinase 3 (FLT3) is implicated in the pathogenesis of acute myeloid leukemia (AML) in 20–30% of patients. In this study we identified a highly selective (phenylethenyl)quinazoline compound family as novel potent inhibitors of the FLT3-ITD and FLT3-D835Y kinases. Their prominent effects were confirmed by biochemical and cellular proliferation assays followed by mice xenograft studies. Our modelling experiments and the chemical structures of the compounds predict the possibility of covalent inhibition. The most effective compounds triggered apoptosis in FLT3-ITD AML cells but had either weak or no effect in FLT3-independent leukemic and non-leukemic cell lines. Our results strongly suggest that our compounds may become therapeutics in relapsing and refractory AML disease harboring various ITD and tyrosine kinase domain mutations, by their ability to overcome drug resistance.

NOVEL BENZYLAMINO SUBSTITUTED QUINAZOLINES AND DERIVATIVES AS SOS1 INHIBITORS

The present invention encompasses compounds of formula (I), wherein the groups R1 to R7 have the meanings given in the claims and specification, their use as inhibitors of SOS1, pharmaceutical compositions which contain compounds of this kind and their use as medicaments/medical uses, especially as agents for treatment and/or prevention of oncological diseases.

Synthesis and biological evaluation of novel quinazoline-4-piperidinesulfamide derivatives as inhibitors of NPP1

The ecto-nucleotide pyrophosphatase/phosphodiesterase-1 (NPP1) was recently shown to promote mineralization of the aortic valve, hence, its inhibition represents a significant target. A quinazoline-4-piperidine sulfamide compound (QPS1) has been described as a specific and non-competitive inhibitor of NPP1. We report herein the synthesis and in vitro inhibition studies of novel quinazoline-4-piperidine sulfamide analogues using QPS1 as the lead compound. Of the 26 derivatives prepared, four compounds were found to have Ki 105 nM against human NPP1.

2-METHYL-QUINAZOLINES

The present invention describes 2-methyl-quinazoline compounds of general formula (I), methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds, and the use of said compounds for manufacturing pharmaceutical compositions. The 2-methyl substituted quinazoline compounds of general formula(I) effectively and selectively inhibit the Ras-Sos interaction without significantly targeting the EGFR receptor. They are therefore useful for the treatment or prophylaxis of diseases, in particular of hyperproliferative disorders, such as cancer as a sole agent or in combination with other active ingredients.

STYRYL QUINAZOLINE DERIVATIVES AS PHARMACEUTICALLY ACTIVE AGENTS

The present invention relates to styryl quinazoline derivatives of the general formula (I) and pharmaceutically acceptable solvates, hydrates, salts, regioisomeric and polymorphic forms thereof as well as pharmaceutical compositions containing at least on

Synthesis and evaluation of quinazolines as inhibitors of the bacterial cell division protein FtsZ

The bacterial cell division protein FtsZ is one of many potential targets for the development of novel antibiotics. Recently, zantrin Z3 was shown to be a cross-species inhibitor of FtsZ; however, its specific interactions with the protein are still unknown. Herein we report the synthesis of analogues that contain a more tractable core structure and an analogue with single-digit micromolar inhibition of FtsZs GTPase activity, which represents the most potent inhibitor of Escherichia coli FtsZ reported to date. In addition, the zantrin Z3 core has been converted to two potential photo-cross-linking reagents for proteomic studies that could shed light on the molecular interactions between FtsZ and molecules related to zantrin Z3.

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.