731-52-2

Usage

Uses

Used in Pharmaceutical Industry:
2,4(1H,3H)-Quinazolinedione, 3-phenyl-, 2-hydrazone is used as a potential drug candidate for its anti-tumor properties. It has been studied for its ability to inhibit the growth and proliferation of cancer cells, making it a promising agent for the development of anti-cancer therapies.
2,4(1H,3H)-Quinazolinedione, 3-phenyl-, 2-hydrazone is also used as a potential drug candidate for its anti-inflammatory properties. Its ability to modulate inflammatory responses and reduce inflammation makes it a valuable compound for the development of anti-inflammatory medications.
In addition to its direct therapeutic applications, 2,4(1H,3H)-Quinazolinedione, 3-phenyl-, 2-hydrazone can also be used as a building block or intermediate in the synthesis of other pharmaceutical compounds. Its unique structure and functional groups can be further modified or combined with other molecules to create new drugs with improved efficacy and selectivity.
Overall, 2,4(1H,3H)-Quinazolinedione, 3-phenyl-, 2-hydrazone is a versatile and promising compound in the field of medicinal chemistry, with potential applications in the development of anti-cancer and anti-inflammatory drugs, as well as in the synthesis of other pharmaceutical agents. Further research and development are needed to fully explore its potential and optimize its therapeutic properties.

Upstream product

• 18741-24-7 3-phenyl-2-thioxo-2,3-dihydro-1H-quinazolin-4-one 
• 727-62-8 2-chloro-3-phenylquinazoline-4-(3H)-one 
• 73987-32-3 2-methylmercapto-3-phenyl-4(3H)-quinazolinone 
• 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 
• 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 
• 18418-42-3 phenyl-dithiocarbamic acid; sodium salt 
• 62-53-3 aniline 
• 603-23-6 3-phenyl-2,4-(1H,3H)-quinazolinedione 
• 96221-91-9 N-o-Carbomethoxyphenyl-N'-phenylthiourea 

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 
• 86842-55-9 1-(4-methoxyphenyl)-4-phenyl-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 

Relevant academic research and scientific papers

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.

Design, synthesis, and pharmacological characterization of some 2-substituted-3-phenyl-quinazolin-4(3H)-one derivatives as phosphodiesterase inhibitors

Some 3-phenyl-quinazolin-4(3H)-one-2-thioethers (3a–e, 5a,b, 7a–e, 9a–d, 10a–d, and 12) along with 2-aminoquinazoline derivatives 13a–c were prepared and screened for their in vitro phosphodiesterase (PDE) inhibitory activity. Some compounds such as 7d,e,

Anti-HIV, Antitubercular and Antibacterial Activities of Novel 3-(Substituted Quinazolinylamino)-2-phenyl quinazolin-4(3H)ones

In the present study, we have synthesized a series of novel 2-phenyl-3-(substituted quinazolinylamino)quinazolin-4(3H)-ones by the reaction of 3-(substituted)-2-hydrazinoquinazoline-4(3H)-ones with 2-phenyl-3,1-benzoxazin-4-one. 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, 3-(4-nitrophenyl)-2-(4-oxo-2-phenylquinazolin-3(4H)-ylamino)quinazolin-4(3H)-one (BQZ6) and 3-(4-chlorophenyl)-2-(4-oxo-2-phenylquinazolin-3(4H)-ylamino)quinazolin-4(3H)-one (BQZ7) shown most potent antibacterial activity against E. coli, P. aeruginosa and S. aureus with the MIC of 3 μg/mL. The compound BQZ7 exhibited the antitubercular activity with the MIC of 25 μg/mL and anti-HIV activity with the MIC of 35.4 μg/mL against HIV1 and HIV2 and offers potential lead for further optimization and development to new antitubercular and anti-HIV agents. The results 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.

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.

Synthesis and Anticonvulsant Activity Evaluation of 4-Phenyl-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one and Its Derivatives

A series of 4-(substituted-phenyl)-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-ones (6a-x) with triazole and other heterocyclic substituents (7-14) were synthesized and the compounds were evaluated for their anticonvulsant activity and neurotoxicity by maximal electroshock (MES) and rotarod neurotoxicity tests. Among the compounds studied, 6o and 6q showed wide margins of safety with protective indices (PIs) that were much higher than those of currently used drugs (PI6o > 25.5, PI6q > 26.0). Compounds 6o and 6q showed significant oral activity against MES-induced seizures in mice, with ED50 values of 88.02 and 94.6 mg/kg, respectively. The two compounds were also found to have potent activity against seizures that were induced by pentylenetetrazole and bicuculline. A series of 4-(substituted-phenyl)-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-ones with triazole and other heterocyclic substituents were synthesized and the compounds were evaluated for their anticonvulsant activity and neurotoxicity using maximal electroshock and rotarod neurotoxicity tests.

Green and efficient synthesis of 2-(4-oxo-3,4-dihydroquinazolin-2-yl)-2,3-dihydropthalazine-1,4-dione

2-Hydrazinoquinazolin-3H-4-ones 1a,b were reacts with each of the anhydrides, phthalic anhydride 2a, succinic anhydride 2b and maleic anhydride 2c independently in PEG-600 at RT to yield 2-(2-(4-oxo-3,4-dihydroquinazolin-2-yl)hydrazineecarbonyl) benzoic acid 3a,b, 4-oxo-4-(2-(4-oxo-3,4-dihydroquinazolin-2-yl)hydrazinyl)butanoic acid 3c,d and 4-oxo-4-(2-(4-oxo-3,4-dihydroquinazolin-2-yl)hydrazinyl)but-2-enoic acid 3e,f, respectively. 3a, b, 3c,d, 3e,f have been transformed into 2-(4-oxo-3,4-dihydroquinazolin-2-yl)-2,3-dihydrophthalazine-1,4-dione 4a,b, 1-(4-oxo-3,4-dihydroquinazolin-2-yl)piperazine-3,6-dione 4c,d and 1-(4-oxo-3,4-dihydroquinazolin-2-yl)-1,2-dihydropyridazine-3,6-dione 4e,f, respectively by heating each in PEG-600 at 100°C for 3-3.5 hr in high yields and in high purity, involving a dehydrative ring closure. The final compounds 4a-f have also been prepared alternatively by reacting 1 with 2 in PEG-600 at 100°C for 3.5-4 hr.

Spectral characterization of novel 3-phenyl-2-substituted quinazoline and fused quinazoline derivatives

3-phenyl-2-thioxo-quinazolin-4(3H)one 1 was utilized for the construction of some novel 2-substituted quinazolin-4(3H)one derivatives through the formation of 2-hydrazinyl quinazolinone, which was used as the key starting material for the synthesis of 2-heteryl quinazolines via the reaction with one carbon donors, -diketones and -ketoester. Infrared, 1H NMR, and mass spectra of the synthesized compounds were discussed. Some of them showed promising anti-inflammatory activity. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Copyright Taylor & Francis Group, LLC.

Antimicrobial studies of some novel quinazolinones fused with [1,2,4]-triazole, [1,2,4]-triazine and [1,2,4,5]-tetrazine rings

Three series of novel and new fused heterocyclic systems, viz. triazolo[4,3-a]-quinazolin-7-ones (4), [1,2,4,5]-tetrazino[4,3-a]-quinazolin-8-ones (6) and indolo[2,3-c][1,2,4]-triazino[4,3-a]-quinazolin-8-ones (8) have been synthesized from the key intermediate 3-(substituted-phenyl)-2-hydrazino-quinazolin-4-ones (3). Thus, condensation of (3) with appropriate aromatic acids in the presence of DCC in dichloromethane afforded the fused system (4), while reaction of (3) with isatin in methanol gave the corresponding Schiff base (7) which on cyclodehydration furnished another fused heterocyclic system (8). The intermediate (3) on refluxing with substituted-phenylisothiocyanate gave the substituted-thiosemicarbazide (5), which on oxidative cyclization with bromine in CCl4 furnished the novel fused system (6). The structures of intermediate and final compounds have been determined by means of IR, 1H NMR, 13C NMR, UV and elemental analysis. All the synthesized compounds have been screened for their antibacterial activity against Gram-negative bacteria, Escherichia coli, Pseudomonas aeruginosa and Gram-positive bacteria, Streptococcus pneumoniae, Bacillus subtilis, as well as demonstrated significant antifungal activity against fungi viz. Candida albicans, Aspergillus fumigatus, Aspergillus flavus, and Aspergillus niger.

Tautomerism of guanidines studied by 15N NMR: 2-hydrazono-3-phenylquinazolin-4(3H)-ones and related compounds

2-Hydrazono-3-phenylquinazolin-4(3H)-ones 11a-i are shown by 15N NMR to exist in DMSO solution predominantly as the imino tautomers B and not the amino tautomers A. 2-Hydrazino-benzimidazole derivative 12 and 2-hydrazino-4,6-dimethylpyrimidine derivative 13 were found to exist predominantly as the amino tautomers.