39576-82-4

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Dichloro-6-methylquinazoline is used as a chemical intermediate for the synthesis of various pharmaceuticals, leveraging its unique structure to contribute to the development of new drugs.
Used in Agrochemical Industry:
2,4-DICHLORO-6-METHYLQUINAZOLINE is utilized as an intermediate in the production of agrochemicals, specifically for its herbicidal properties, which can be harnessed to create effective weed control agents for agricultural applications.
Used in Cancer Research:
2,4-Dichloro-6-methylquinazoline is used as a potential anti-cancer agent in research settings, exploring its capacity to treat various types of cancer due to its inherent properties.
Used in Disease Treatment Research:
2,4-DICHLORO-6-METHYLQUINAZOLINE is employed in research aimed at identifying its potential use in the treatment of different diseases, based on its biological activity and the possibility of its integration into therapeutic agents.
Used in Synthesis of Novel Molecules:
2,4-Dichloro-6-methylquinazoline serves as a building block in the synthesis of new molecules with biological activity, indicating its importance in the discovery of innovative chemical entities for various applications.

InChI:InChI=1/C9H6Cl2N2/c1-5-2-3-7-6(4-5)8(10)13-9(11)12-7/h2-4H,1H3

Upstream product

• 2941-78-8 2-Amino-5-methylbenzoic acid 
• 57-13-6 urea 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 5925-93-9 2-amino-5-methylbenzonitrile 
• 784183-53-5 2,2,2-trifluoro-N-(2-iodo-4-methylphenyl)acetamide 
• 29289-13-2 2-iodo-4-methylaniline 
• 150893-79-1 N-(2-cyano-4-methyl-phenyl)-2,2,2-trifluoro-acetamide 
• 503-38-8 trichloromethyl chloroformate 
• 62484-16-6 6-methyl-1H-quinazoline-2,4-dione 

Downstream Products

• 112888-68-3 2,4-Diphenoxy-6-methylquinazoline 
• 62484-42-8 2-Chloro-3,4-dihydro-4-oxo-6-methylquinazoline 
• 186501-13-3 3-(4-Benzhydryl-piperazin-1-ylmethyl)-9-methyl-6H-imidazo[1,2-c]quinazolin-5-one 
• 112888-69-4 6-Bromomethyl-2,4-diphenoxy-quinazoline 
• 112888-66-1 2,4-Bis<2-(benzoyloxy)ethoxy>-6-methylquinazoline 
• 112888-67-2 C₂₇H₂₃BrN₂O₆ 
• 112888-14-9 (S)-2-{4-[(2-Ethoxy-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-pentanedioic acid 
• 112888-16-1 (S)-2-(4-{[2-(2-Hydroxy-ethoxy)-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl]-prop-2-ynyl-amino}-benzoylamino)-pentanedioic acid 
• 112888-15-0 (S)-2-(4-{[2-(2-Methoxy-ethoxy)-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl]-prop-2-ynyl-amino}-benzoylamino)-pentanedioic acid 
• 112888-17-2 (S)-2-{4-[(4-Oxo-2-phenoxy-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-pentanedioic acid 
• 118111-62-9 Diethyl N-<4--N-prop-2-ynylamino>benzoyl>-L-glutamate 
• 118111-85-6 Diethyl N-<4-methyl>-N-prop-2-ynylamino>benzoyl>-L-glutamate 
• 118111-84-5 Diethyl N-<4--N-prop-2-ynylamino>benzoyl>-L-glutamate 
• 118111-87-8 Diethyl N-<4--6-quinazolinyl>methyl>-N-prop-2-ynylamino>benzoyl>-L-glutamate 

Relevant academic research and scientific papers

One-pot cascade ring enlargement of isatin-3-oximes to 2,4-dichloroquinazolines mediated by bis(trichloromethyl)carbonate and triarylphosphine oxide

An efficient and convenient one-pot cascade synthesis of 2,4-dichloroquinazolines directly from isatin-3-oximes with the addition of bis(trichloromethyl)carbonate and triarylphosphine oxide was developed, leading to substituted quinazolines in moderate to excellent yields. The efficiency of this transformation was demonstrated by compatibility with a range of functional groups. Thus, the method represents a convenient and practical strategy for the synthesis of substituted 2,4-dichloroquinazolines.

N2N N4-disubstituted quinazoline-2,4-diamines and uses thereof

Described herein are quinazoline-based compounds and formulations thereof. In some embodiments, the compounds and/or formulations thereof can be effective to inhibit and/or kill A. baumannii. Also described herein are methods of treating a subject in need thereof by administering to the subject in need thereof a quinazoline-based compound and/or formulation thereof to the subject in need thereof.

AMINOISOXAZOLINE COMPOUNDS AS AGONISTS OF ALPHA7-NICOTINIC ACETYLCHOLINE RECEPTORS

The present invention relates to novel aminoisoxazoline compounds, and pharmaceutical compositions of the same, that are suitable as agonists or partial agonists of α7-nAChR, and methods of preparing these compounds and compositions, and the use of these compounds and compositions in methods of maintaining, treating and/or improving cognitive function. In particular, methods of administering the compound or composition to a patient in need thereof, for example a patient with a cognitive deficiency and/or a desire to enhance cognitive function, that may derive a benefit therefrom.

Characterizing the antimicrobial activity of N2,N4-disubstituted quinazoline-2,4-diamines toward multidrug-resistant Acinetobacter baumannii

We previously reported a series of N2,N4-disubstituted quinazoline-2,4- diamines as dihydrofolate reductase inhibitors with potent in vitro and in vivo antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) strains. In this work, we extended our previous study to the Gram-negative pathogen Acinetobacter baumannii. We determined that optimized N2,N4-disubstituted quinazoline-2,4-diamines are strongly antibacterial against multidrug-resistant A. baumannii strains when the 6-position is replaced with a halide or an alkyl substituent. Such agents display potent antibacterial activity, with MICs as low as 0.5 μM, while proving to be strongly bactericidal. Interestingly, these compounds also possess the potential for antibiofilm activity, eradicating 90% of cells within a biofilm at or near MICs. Using serial passage assays, we observed a limited capacity for the development of resistance toward these molecules (4-fold increase in MIC) compared to existing folic acid synthesis inhibitors, such as trimethoprim (64-fold increase) and sulfamethoxazole (128-fold increase). We also identified limited toxicity toward human cells, with 50% lethal doses (LD50s) of ≤23 μM for lead agents 4 and 5. Finally, we demonstrated that our lead agents have excellent in vivo efficacy, with lead agent 5 proving more efficacious than tigecycline in a murine model of A. baumannii infection (90% survival versus 66%), despite being used at a lower dose (2 versus 30 mg kg-1). Together, our results demonstrate that N2,N4-disubstituted quinazoline-2,4-diamines have strong antimicrobial and antibiofilm activities against both Gram-positive organisms and Gram-negative pathogens, suggesting strong potential for their development as antibacterial agents.

Synthesis and Antibacterial Activity of Sulfur-linked Bis and Tris Heterocycles

The bis and tris heterocycles-benzoxazolyl/benzothiazolyl/benzimidazolyl quinazolines linked by sulfur and/or nitrogen were prepared from 2,4-dichloroquinazoline and benzazolyl-2-thiol/benzazolyl-2-amine and studied their antibacterial activity. The nitro-substituted sulfur-linked bisbenzothiazolylquinazoline (12f), bisbenzimidazolylquinazoline (13f), and nitro-substituted sulfur and nitrogen-linked bisbenzothiazolylquinazoline (15f) were found to be potential antibacterial agents against Staphylococcus aureus.

Octahydropyrrole[3, 4-c]pyrrole derivative and using method and application thereof

The invention relates to an ctahydropyrrole[3, 4-c]pyrrole derivative and a using method and application thereof. A compound and a drug composition containing the same are used for resisting orexin receptors. The invention further relates to methods of pr

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.

Synthesis and antimicrobial activity of amino linked heterocycles

Amino-linked benzoxazolyl/benzothiazolyl/benzimidazolyl quinazolines were prepared and their antimicrobial activity studied. The nitro-substituted benzothiazolyl quinazoline (8f) may be a potential antibacterial agent against Staphylococcus aureus and nitro-substituted benzimidazolyl quinazoline (9f) may be a potential antifungal agent against Aspergillus niger.

Antileishmanial activity of a series of N2, N 4-disubstituted quinazoline-2,4-diamines

A series of N2,N4-disubstituted quinazoline-2,4- diamines has been synthesized and tested against Leishmania donovani and L. amazonensis intracellular amastigotes. A structure-activity and structure-property relationship study was conducted in part using the Topliss operational scheme to identify new lead compounds. This study led to the identification of quinazolines with EC50 values in the single digit micromolar or high nanomolar range in addition to favorable physicochemical properties. Quinazoline 23 also displayed efficacy in a murine model of visceral leishmaniasis, reducing liver parasitemia by 37% when given by the intraperitoneal route at 15 mg kg-1 day-1 for 5 consecutive days. Their antileishmanial efficacy, ease of synthesis, and favorable physicochemical properties make the N2,N 4-disubstituted quinazoline-2,4-diamine compound series a suitable platform for future development of antileishmanial agents.

Ligand based design of novel histamine H4 receptor antagonists; Fragment optimization and analysis of binding kinetics

The histamine H4 receptor is a G protein-coupled receptor that has attracted much interest for its role in inflammatory and immunomodulatory functions. In our search for new H4R ligands, a low affinity isoquinoline fragment was optimized to 7-(furan-2-yl)-4-(piperazin-1-yl) quinazolin-2-amine (VUF11489), as a new H4R antagonist. Analysis of its binding kinetics at the human H4R showed this compound to have a very different dissociative half-life in comparison with reference antagonist JNJ7777120.