50377-49-6

Usage

Uses

Used in Scientific Research:
4-chloro-6,7-dimethoxy-2-methylquinazoline is used as a research chemical for the study of its properties and potential applications in various fields of chemistry and related sciences. Its unique molecular structure with a chlorine atom, two methoxy groups, and a methyl group may offer insights into the behavior of similar compounds and contribute to the development of new chemical entities.
Used in Pharmaceutical Development:
Although not explicitly mentioned, the compound's structure suggests that it could be used as a starting material or intermediate in the synthesis of pharmaceutical compounds. The presence of a quinazoline core is common in many drugs, and the additional functional groups may provide opportunities for further modification to explore potential therapeutic applications.
Used in Chemical Synthesis:
4-chloro-6,7-dimethoxy-2-methylquinazoline may be used as a building block in the synthesis of more complex organic molecules. Its unique structure could be a valuable component in the creation of novel compounds with specific properties, such as improved stability, reactivity, or selectivity in chemical reactions.
Used in Material Science:
4-chloro-6,7-dimethoxy-2-methylquinazoline's aromatic and heterocyclic nature may make it a candidate for use in the development of new materials with specific properties, such as conductivity, magnetism, or optical characteristics. Its potential applications in material science could be explored through further research and experimentation.

InChI:InChI=1/C11H11ClN2O2/c1-6-13-8-5-10(16-3)9(15-2)4-7(8)11(12)14-6/h4-5H,1-3H3

Upstream product

• 35241-23-7 6,7-dimethoxy-2-methylquinazoline-4(3H)-one 
• 26759-46-6 methyl 2-amino-4,5-dimethoxybenzoate 
• 35241-23-7 6,7-dimethoxy-2-methylquinazolin-4-ol 
• 63190-57-8 methyl 2-acetamido-4,5-diemthoxy benzoate 
• 5653-40-7 2-Amino-4,5-dimethoxybenzoic acid 

Downstream Products

• 849218-01-5 6,7-dimethoxy-2-methyl-4-(4-nitro-phenoxy)-quinazoline 
• 849218-02-6 4-(6,7-dimethoxy-2-methyl-quinazolin-4-yloxy)-phenylamine 
• 849218-00-4 N-(4-fluorophenyl)-N'-(4-{[2-methyl-6,7-bis(methyloxy)quinazolin-4-yl]oxy}phenyl)cyclopropane-1,1-dicarboxamide 

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.

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.

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.

SMALL MOLECULE AGONISTS OF NEUROTENSIN RECEPTOR 1

Provided herein are small molecule neurotensin receptor agonists, compositions comprising the compounds, and methods of using the compounds and compositions comprising the compounds.

SUBSTITUTED 4-(SELENOPHEN-2(OR-3)-YLAMINO)PYRIMIDINE COMPOUNDS AND METHODS OF USE THEREOF

Selenophene compounds of formula (I) are described herein. In the compounds of Formula (I), ring A is a 6-membered aromatic fused ring, optionally containing one, two or three nitrogen atoms; a 5-membered heteroaromatic fused ring; or a mono- or bicyclic

Discovery of ML314, a brain penetrant nonpeptidic β-arrestin biased agonist of the neurotensin NTR1 receptor

The neurotensin 1 receptor (NTR1) is an important therapeutic target for a range of disease states including addiction. A high-throughput screening campaign, followed by medicinal chemistry optimization, led to the discovery of a nonpeptidic β-arrestin biased agonist for NTR1. The lead compound, 2-cyclopropyl-6,7-dimethoxy-4-(4-(2-methoxyphenyl)-piperazin-1-yl)quinazoline, 32 (ML314), exhibits full agonist behavior against NTR1 (EC50 = 2.0 μM) in the primary assay and selectivity against NTR2. The effect of 32 is blocked by the NTR1 antagonist SR142948A in a dose-dependent manner. Unlike peptide-based NTR1 agonists, compound 32 has no significant response in a Ca2+ mobilization assay and is thus a biased agonist that activates the β-arrestin pathway rather than the traditional Gq coupled pathway. This bias has distinct biochemical and functional consequences that may lead to physiological advantages. Compound 32 displays good brain penetration in rodents, and studies examining its in vivo properties are underway.

C-MET MODULATORS AND METHODS OF USE

The present invention provides compounds for modulating protein kinase enzymatic activity for modulating cellular activities such as proliferation, differentiation, programmed cell death, migration and chemoinvasion. More specifically, the invention provides quinazolines and quinolines which inhibit, regulate and/or modulate kinase receptor, particularly c-Met, KDR, c-Kit, flt-3 and flt-4, signal transduction pathways related to the changes in cellular activities as mentioned above, compositions which contain these compounds, and methods of using them to treat kinase-dependent diseases and conditions. The present invention also provides methods for making compounds as mentioned above, and compositions which contain these compounds.

Syntheses of Some 4-Anilinoquinazoline Derivatives

Some 4-N-(3′- or 4′-substituted-phenyl)amino-6,7- dimethoxyquinazolines and the corresponding unsubstituted compounds were synthesized from 2-amino-4,5-dimethoxybenzoic acid and the appropriate substituted anilines. Other related quinazolines or their synthetic intermediates were also obtained. A large number of the described quinazolines are new compounds, while the remaining were prepared by a more efficient procedure. The main goal for the synthesis of these compounds comes from the fact that the 4-anilinoquinazoline pharmacophore is an important unit, which is found among the ATP-competitive inhibitors of several protein kinase enzymes.

Tyrosine kinase inhibitors. 8. An unusually steep structure-activity relationship for analogues of 4-(3-bromoanilino)-6,7-dimethoxyquinazoline (PD 153035), a potent inhibitor of the epidermal growth factor receptor

4-(3-Bromoanilino)-6,7-dimethoxyquinazoline (32, PD 153035) is a very potent inhibitor (IC50 0.025 nM) of the tyrosine kinase activity of the epidermal growth factor receptor (EGFR), binding competitively at the ATP site. Structure-activity relationships for close analogues of 32 are very steep. Some derivatives have IC50s up to 80-fold better than predicted from simple additive binding energy arguments, yet analogues possessing combinations of similar phenyl and quinazoline substituents do not show this 'supra-additive' effect. Because some substituents which are mildly deactivating by themselves can be strongly activating when used in the correct combinations, it is proposed that certain substituted analogues possess the ability to induce a change in the conformation of the receptor when they bind. There is some bulk tolerance for substitution in the 6- and 7-positions of the quinazoline, so that 32 is not the optimal inhibitor for the induced conformation. The diethoxy derivative 56 [4-(3-bromoanilino)- 6,7-diethoxy-quinazoline] shows an IC50 of 0.006 nM, making it the most potent inhibitor of the tyrosine kinase activity of the EGFR yet reported.