2400-95-5

Basic information

• Product Name: 3-(4-Chlorophenyl)quinazoline-2,4(1H,3H)-dione
• Synonyms: 3-(4-Chlorophenyl)quinazoline-2,4(1H,3H)-dione;3-(4-chlorophenyl)-1H-quinazoline-2,4-dione;3-(4-chlorophenyl)-1H-quinazoline-2,4-quinone
• CAS NO: 2400-95-5
• Molecular Formula: C₁₄H₉ClN₂O₂
• Molecular Weight: 272.68646
• Mol File: 2400-95-5.mol
• Article Data: 16

Chemical Properties

• Melting Point: 268-271 °C
• Appearance: /
• Density: 1.416±0.06 g/cm3(Predicted)
• PKA: 12.25±0.20(Predicted)
• CAS DataBase Reference: 3-(4-Chlorophenyl)quinazoline-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-Chlorophenyl)quinazoline-2,4(1H,3H)-dione(2400-95-5)
• EPA Substance Registry System: 3-(4-Chlorophenyl)quinazoline-2,4(1H,3H)-dione(2400-95-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 2400-95-5(Hazardous Substances Data)

Upstream product

• 118-48-9 isatoic anhydride 
• 49802-15-5 diethyl (4-chlorophenyl)phosphoramidate 
• 19959-41-2 methyl 2-[3-(4-chlorophenyl)ureido]benzoate 
• 79860-14-3 N-(4-Chloro-phenyl)-2-(3,3-dimethyl-ureido)-benzamide 
• 81541-40-4 R,S-N-(<3-<4-Chlorphenyl>-3,4-dihydro-4-oxo-2-chinazolinyl>-hydroxymethyl)acetamid 
• 201230-82-2 carbon monoxide 
• 615-43-0 2-iodophenylamine 
• 104-12-1 p-chlorphenylisocyanate 
• 57644-24-3 3-[(4-chlorophenyl)imino]-1,3-dihydro-2H-indol-2-one 
• 106-47-8 4-chloro-aniline 
• 57-13-6 urea 
• 81552-42-3 R,S-Essigsaeure(acetamido-<3-<4-chlorphenyl>-3,4-dihydro-4-oxo-2-chinazolinyl>-methyl)ester 
• 80096-31-7 2-Azidomethyl-3-(4-chlorphenyl)-3,4-dihydro-4-chinazolinon 
• 22280-87-1 2-(chloromethyl)-3-(4-chlorophenyl)quinazolin-4(3H)-one 

Downstream Products

• 16081-94-0 3-(4-chlorophenyl)quinazoline-2,4(1H,3H)-dithione 
• 925016-67-7 1-[2-(3,4-dimethoxyphenyl)-2-oxoethyl]-3-(4-chlorophenyl)quinazoline-2,4-dione 
• 1228963-55-0 3-(4-chlorophenyl)-1-(4-chlorophenylsulfonyl)quinazoline-2,4(1H,3H)-dione 
• 1228963-54-9 3-(4-chlorophenyl)-1-phenylsulfonylquinazoline-2,4(1H,3H)-dione 
• 1228963-56-1 3-(4-chlorophenyl)-1-(4-methylphenylsulfonyl)quinazoline-2,4(1H,3H)-dione 
• 115540-75-5 1-methyl-3-(4-chlorophenyl)quinazolin-2,4(1H,3H)-dione 
• 1028-40-6 3-(4-chlorophenyl)-2-thioxo-2,3-dihydro-1H-quinazolin-4-one 

Relevant articles and documents

Synthesis, 2D-QSAR studies and biological evaluation of quinazoline derivatives as potent anti-trypanosoma cruzi agents

Background: Chagas disease affects about 7 million people worldwide. Only two drugs are currently available for the treatment for this parasite disease, namely, benznidazol (Bzn) and nifurtimox (Nfx). Both drugs have limited curative power in the chronic phase of the disease. Therefore, continuous research is an urgent need so as to discover novel therapeutic alternatives. Objective: The development of safer and more efficient therapeutic anti-T. cruzi drugs continues to be a major goal in trypanocidal chemotherapy. Method: Synthesis, 2D-QSAR and drug-like physicochemical properties of a set of quinazolinone and quinazoline derivatives were studied as trypanocidal agents. All compounds were screened in vitro against Trypanosoma cruzi (Tulahuen strain, Tul 2 stock) epimastigotes and bloodstream trypomastigotes. Results: Out of 34 compounds synthesized and tested, six compounds (5a, 5b, 9b, 9h, 13f and 13p) displayed significant activity against both epimastigotes and tripomastigotes, without exerting toxicity on Vero cells. Conclusion: The antiprotozoal activity of these quinazolinone and quinazoline derivatives represents an interesting starting point for a medicinal chemistry program aiming at the development of novel chemotherapies for Chagas disease.

Oxidative Rearrangement of Isatins with Arylamines Using H2O2 as Oxidant: A Facile Synthesis of Quinazoline-2,4-diones and Evaluation of Their Antibacterial Activity

A green and highly efficient synthetic method for the synthesis of quinazoline-2,4-diones with hydrogen peroxide as the terminal oxidant has been developed. The reaction features the mild reaction conditions, broad substrate scope, metal-free catalysts, and sole byproduct water. A plausible mechanism for this process was proposed. Moreover, an antibacterial activity study was performed to evaluate the antimicrobial activities towards two Gram-negative bacterial strains (Escherichia coli, and Klebsiella pneumonia) and two Gram-positive bacterial strains (Staphylococcus epidermidis, and Staphylococcus aureus) using the Broth microdilution method.

Specific inhibitors of puromycin-sensitive aminopeptidase with a 3-(halogenated phenyl)-2,4(1H,3H)-quinazolinedione skeleton

Specific puromycin-sensitive aminopeptidase (PSA) inhibitors with a 3-(halogenated phenyl)-2,4(1H,3H)-quinazolinedione skeleton were prepared and their structure-activity relationships were investigated. The nature (F, Cl or Br), number and position(s) of the halogen atom(s) introduced into the 3-phenyl group were concluded to be critical determinants of the inhibitory activity.