25171-19-1

Basic information

• Product Name: 2,4-DICHLORO-1,2,3,4-TETRAHYDRO-7-METHYLQUINAZOLINE
• Synonyms: 2,4-Dichloro-7-methylquinazoline;2,4-DICHLORO-1,2,3,4-TETRAHYDRO-7-METHYLQUINAZOLINE
• CAS NO: 25171-19-1
• Molecular Formula: C₉H₆Cl₂N₂
• Molecular Weight: 213.06
• Mol File: 25171-19-1.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 226.8°C at 760 mmHg
• Flash Point: 112.678°C
• Appearance: /
• Density: 1.419g/cm³
• Vapor Pressure: 0.121mmHg at 25°C
• Refractive Index: 1.652
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -0.15±0.30(Predicted)
• CAS DataBase Reference: 2,4-DICHLORO-1,2,3,4-TETRAHYDRO-7-METHYLQUINAZOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DICHLORO-1,2,3,4-TETRAHYDRO-7-METHYLQUINAZOLINE(25171-19-1)
• EPA Substance Registry System: 2,4-DICHLORO-1,2,3,4-TETRAHYDRO-7-METHYLQUINAZOLINE(25171-19-1)

Safety Data

• Hazardous Substances Data: 25171-19-1(Hazardous Substances Data)

Usage

General Description

2,4-Dichloro-1,2,3,4-tetrahydro-7-methylquinazoline is a chemical compound. Its structure involves a quinazoline core, which is a sort of bicyclic aromatic ring. Notably, it includes two chlorine atoms and one methyl group. As a derivative of quinazoline, it's likely to have interesting biological properties and could potentially be useful in pharmaceutical development. As a relatively complex organic molecule, it's synthesis and reactions could be of interest to the fields of organic and medicinal chemistry. Further study would be required to ascertain specific properties, toxicity, potential uses, and safety information.

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

Upstream product

• 62484-15-5 7-methylquinazoline-2,4-(1H,3H)-dione 
• 39549-79-6 2-amino-4-methylbenzamide 
• 2305-36-4 4-methylanthranilic acid 

Downstream Products

• 1039736-58-7 2-chloro-7-methyl-N-[(1S)-1-(4-nitrophenyl)ethyl]quinazolin-4-amine 
• 1039736-86-1 (4-{4-[(2-chloro-7-methyl-quinazolin-4-ylamino)-methyl]-phenylcarbamoyl}-piperidine-1-carboxylic acid tert-butyl ester) 
• 1039736-87-2 (4-(tert-butoxycarbonyl-{4-[(2-chloro-7-methyl-quinazolin-4-ylamino)-methyl]-phenyl}-aminocarbonyl)-piperidine-1-carboxylic acid tert-butyl ester) 
• 1039736-54-3 (2-chloro-7-methyl-quinazolin-4-yl)-(4-nitro-benzyl)-amine 
• 1039736-47-4 N-(4-{[(2-chloro-7-methylquinazolin-4-yl)amino]methyl}phenyl)-4-fluorobenzamide 
• 1039736-11-2 1-benzyl-N-(4-{[(2-chloro-7-methylquinazolin-4-yl)amino]methyl}phenyl)piperidine-4-carboxamide 
• 1039736-32-7 N-(4-bromophenyl)-N'-[4-({[2-(chloro)-7-methylquinazolin-4-yl]amino}methyl)phenyl]urea 
• 1039736-33-8 N-(4-flourophenyl)-N'-[4-({[2-(chloro)-7-methylquinazolin-4-yl]amino}methyl)phenyl]urea 
• 1039736-30-5 N-(4-chlorophenyl)-N'-[4-({[2-(chloro)-7-methylquinazolin-4-yl]amino}methyl)phenyl]urea 
• 1039736-49-6 4-bromo-N-(4-((2-chloro-7-methylquinazolin-4-ylamino)methyl)phenyl)benzamide 
• 1039736-50-9 N-(4-{[(2-chloro-7-methylquinazolin-4-yl)amino]methyl}phenyl)-6-methylnicotinamide 
• 1039736-64-5 (S)-6-chloro-N-(4-(1-(2-chloro-7-methylquinazolin-4-ylamino)ethyl)phenyl)nicotinamide 
• 1039734-16-1 N-[4-({[2-(dimethylamino)-7-methylquinazolin-4-yl]amino}methyl)phenyl]-4-fluorobenzamide 
• 1039736-60-1 N₄-[(1S)-1-(4-aminophenyl)ethyl]-N₂,N₂,7-trimethylquinazoline-2,4-diamine 

Relevant articles and documents

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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.