731-52-2

Basic information

• Product Name: 2,4(1H,3H)-Quinazolinedione, 3-phenyl-, 2-hydrazone
• CAS NO: 731-52-2
• Molecular Formula: C14H12N4O
• Molecular Weight: 252.275
• Mol File: 731-52-2.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: 2,4(1H,3H)-Quinazolinedione, 3-phenyl-, 2-hydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4(1H,3H)-Quinazolinedione, 3-phenyl-, 2-hydrazone(731-52-2)
• EPA Substance Registry System: 2,4(1H,3H)-Quinazolinedione, 3-phenyl-, 2-hydrazone(731-52-2)

Safety Data

• Hazardous Substances Data: 731-52-2(Hazardous Substances Data)

Usage

General Description

2,4(1H,3H)-Quinazolinedione, 3-phenyl, 2-hydrazone is a chemical compound with the molecular formula C14H10N4O2. It is a quinazolinedione derivative with a phenyl and hydrazone functional group attached to the nitrogen atom. 2,4(1H,3H)-Quinazolinedione, 3-phenyl-, 2-hydrazone has been studied for its potential biological and pharmaceutical applications, including its anti-tumor and anti-inflammatory properties. Its structure and properties make it a potential candidate for drug development and further research in the field of medicinal chemistry.

Upstream product

• 62-53-3 aniline 
• 118-92-3 anthranilic acid 
• 103-72-0 phenyl isothiocyanate 
• 29745-27-5 3-phenyl-2-ethylsulfanyl-2,3-dihydroquinazolin-4(1H)-one 
• 79785-97-0 hydrazine hydrate 
• 18741-24-7 2-mercapto-3-phenyl-3H-quinazolin-4-one 
• 18418-42-3 phenyl-dithiocarbamic acid; sodium salt 
• 307325-55-9 2‐{[2‐(4‐chlorophenyl)‐2‐oxoethyl]thio}‐3‐phenylquinazolin‐4(3H)‐one 
• 30531-14-7 2‐{[2‐(4‐bromophenyl)‐2‐oxoethyl]thio}‐3‐phenylquinazolin‐4(3H)‐one 
• 603-23-6 3-phenyl-2,4-(1H,3H)-quinazolinedione 
• 96221-91-9 N-o-Carbomethoxyphenyl-N'-phenylthiourea 
• 701-73-5 methyl N-phenyldithiocarbamate 
• 18741-24-7 3-phenyl-2-thioxo-2,3-dihydro-1H-quinazolin-4-one 
• 73987-32-3 2-methylmercapto-3-phenyl-4(3H)-quinazolinone 

Downstream Products

• 77437-08-2 C₂₂H₁₉N₅OS 
• 3318-07-8 benzaldehyde (4-oxo-3-phenyl-3,4-dihydro-2-quinazolinyl)hydrazone 
• 86848-87-5 1,4-diphenyl-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one 
• 68357-48-2 1-methyl-4-phenyl-1,2,4-triazolo<4,3-a>quinazolin-5(4H)-one 
• 66679-85-4 2-(2-(4-chlorobenzylidene)hydrazinyl)-3-phenylquinazolin-4(3H)-one 
• 305850-37-7 2-(N'-4-nitrobenzylidenehydrazino)-3-phenyl-3H-quinazolin-4-one 
• 86842-51-5 2-(N'-4-methoxybenzylidenehydrazino)-3-phenyl-3H-quinazolin-4-one 
• 1147999-68-5 D-mannose N-(3-phenyl-4-oxo-3,4-dihydroquinazolin-2-yl)hydrazone 
• 1147999-70-9 D-ribose N-(3-phenyl-4-oxo-3,4-dihydroquinazolin-2-yl)hydrazone 
• 1146963-29-2 4-phenyl-1-o-tolyl-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one 
• 67443-03-2 3-(phenyl)-2-[4-(phenyl)-thiosemicarbazone]-quinazolin-4-one 
• 1146963-27-0 3-(phenyl)-2-[4-(4-methoxyphenyl)-thiosemicarbazone]-quinazolin-4-one 
• 175688-59-2 3-(phenyl)-2-[4-(4-methylphenyl)-thiosemicarbazone]-quinazolin-4-one 
• 1146963-30-5 1-(2-chlorophenyl)-4-phenyl-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one 

Relevant articles and documents

Anti-HIV and Antibacterial Activities of Novel 2-(3-Substituted-4-oxo-3,4-dihydroquinazolin-2-yl)-2,3-dihydrophthalazine-1,4-diones

Abstract: In the present study, we have synthesized a series of novel 2-(3-substituted-4-oxo-3,4-dihydroquinazolin-2-yl)-2,3-dihydrophthalazine-1,4-diones by the reaction of 3-(substituted)-2-hydrazino-quinazoline-4(3H)-ones with phthalic anhydride. The starting material 3-(substituted)-2-hydrazino-quinazolin-4(3H)-ones were synthesized from various primary amines. All the synthesized compounds were screened for their antitubercular, anti-HIV and antibacterial activity against different gram positive and gram negative strains by agar dilution method. Among the test compounds, 2-(3-(4-chlorophenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)-2,3-dihydrophthalazine-1,4-dione (QCT7) shown most potent antibacterial activity against E. coli, and S. aureus with the MIC of 3 μg/mL. The compound QCT7 exhibited the antitubercular activity with the MIC of 25 μg/mL and anti-HIV activity with the EC50 of 43.68 μM against HIV1 and HIV2 and offers potential lead for further optimization and development to new antitubercular and anti-HIV agents. The results obtained from this study confirm that the synthesized and biologically evaluated quinazolines showed promising antimicrobial, antitubercular and anti-HIV activities and are new scaffolds for antimicrobial activity.

Synthesis, biological evaluation and molecular docking studies of novel quinazolinones as antitubercular and antimicrobial agents

In the present study, a series of novel quinazolinone hybrids, viz. triazepino-quinazolinones 4, thiazolo-triazolo-quinazolinones 7 and triazolo-quinazolinones 8 have been synthesized from the key intermediate 3-(substituted phenyl)-2-hydrazinoquinazolin-4(3H)-ones 3. All the newly synthesized compounds were characterized by means of spectral (IR, 1H NMR, 13C NMR) and elemental analysis. The target compounds were biologically screened for their in vitro antimicrobial and antitubercular activities against pathogenic strain. The results of bioassay demonstrated that some of the compounds exhibited pronounced antimicrobial activity comparable to that of standard drugs tested under similar conditions. Compounds 4c, 4e, 7e and 8b showed relatively very good inhibitory activity against pathogenic bacteria with minimum inhibitory concentration (MIC) of 2.6 μg/mL, 5.2 μg/mL, while the rest of the compounds showed moderate activity. Compounds 4c and 8b were found to be nearly equipotent with ciprofloxacin against P. aeruginosa with MIC 5.2 μg/mL, while compound 8b was more potent against pathogenic bacteria S. aureus. It is very remarkable that four compounds, 4c, 4e, 7e and 8b showed pronounced antifungal activity against selected pathogenic fungi, A. niger, C. albicans with MIC 2.6 μg/mL and 5.2 μg/mL. The antitubercular activity of synthesized compounds reveal that compound 8b showed better activity than the other compounds with a MIC of 5.2 μg/mL against M. tuberculosis (H37Rv). Molecular docking studies of the compounds were performed to rationalize the inhibitory properties of these compounds and results showed that these compounds have good binding energy and better binding affinity within the active pocket, thus these compounds may be considered as potent inhibitors towards selective targets.

Identification of potent cholecystokinin-B receptor antagonists: Synthesis, molecular modeling and anti-cancer activity against pancreatic cancer cells

Advanced malignant stages of pancreatic cancer have poor prognosis and very few treatment strategies are available. Pancreatic cancer is known to possess unique growth-related receptors that when activated, stimulate tumour proliferation. Gastrin and its related peptide cholecystokinin (CCK) are also significantly involved in the growth of this cancer type as well as other malignancies through activation of the cholecystokinin-B receptor (CCK-BR). New treatment strategies with CCK-BR antagonists are being suggested that suppress the growth promoting effects of gastrin. In this paper, we report the development of two series of quinazolinone derivatives incorporating hydrazinecarbothioamide (compounds 3a-g) and the hydrazino group (compounds 4a-e) as linkers for developing CCK-BR antagonists. The affinities of the compounds were determined using docking into the CCK-BR homology modeled structure. The compounds were tested for in vitro CCK-BR binding and gastric acid secretion in an isolated lumen-perfused mouse stomach assay. The compounds exhibited CCK-BR binding activity (IC50) in the range of 0.2-975 nM and showed good gastric acid secretion inhibitory activity. Molecular modeling of the compounds was done and pharmacophore mapping results showed good prediction of in vitro activity which correlated well with the experimental antagonistic activity. The compounds were further tested for their cytotoxicity on CCK-BR expressing pancreatic cancer cells. The results of the study provided two potent CCK-BR antagonists which also possess good to moderate growth inhibitory activities against pancreatic cancer cells.