66679-65-0

Upstream product

• 118-92-3 anthranilic acid 
• 622-59-3 1-isothiocyanato-4-methylbenzene 
• 106-49-0 p-toluidine 
• 37641-50-2 2-Mercapto-3-(4-methylphenyl)-3,4-dihydroquinazolin-4-one 
• 97945-04-5 2-(3-p-Tolyl-thioureido)-benzoic acid methyl ester 
• 53278-69-6 sodium p-methylanilinedithiocarbamate 
• 13037-22-4 methyl (N-(4-methylphenyl))dithiocarbamate 
• 37641-50-2 3-(4-methylphenyl)-2-thioxoquinazolin-4-one 
• 70335-70-5 2-methylthio-3-(4-methylphenyl)quinazolin-4(3H)-one 

Downstream Products

• 77437-16-2 C₂₃H₂₁N₅OS 
• 85772-63-0 1-ethyl-4-(4-methylphenyl)-1,2,4-triazolo[4,3-a]quinazolin-5(4H)-one 
• 87465-28-9 2-[(4-Oxo-3-p-tolyl-3,4-dihydro-quinazolin-2-yl)-hydrazono]-propionic acid 
• 77437-13-9 C₁₉H₁₉N₅OS 
• 67811-48-7 4-(4-methylphenyl)-1,2,4-triazolo[4,3-a]quinazolin-5(4H)-one 
• 1146963-32-7 1-o-tolyl-4-p-tolyl-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one 
• 67443-05-4 3-(4-methylphenyl)-2-[4-(phenyl)-thiosemicarbazone]-quinazolin-4-one 
• 1146963-31-6 1-phenyl-4-p-tolyl-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one 
• 1146963-28-1 3-(4-methylphenyl)-2-[4-(4-methylphenyl)-thiosemicarbazone]-quinazolin-4-one 
• 1146963-33-8 1-(2-chlorophenyl)-4-p-tolyl-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one 
• 1262235-81-3 C₁₆H₁₃N₅O 
• 77437-32-2 2-{N'-[3-Allyl-4-phenyl-3H-thiazol-(2Z)-ylidene]-hydrazino}-3-p-tolyl-3H-quinazolin-4-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.

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.

Cynogen bromide and ethylacetoacetate in heterocyclization: Novel synthesis of tetracyclic derivative of 3-aryl quinazolinones

(Chemical Equation Presented) In this work, tricyclic 1-amino-4- (substituted phenyl)[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one 3 was synthesized by treatment of 2-hydrazinyl-3-(substituted phenyl)quinazolin-4(3H)-one 2 with cyanogen bromide, which on cyc

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.

Synthesis and pharmacological evaluation of some 3-(4-methylphenyl)-2- substituted amino-3H-quinazolin-4-ones as analgesic and anti-inflammatory agents

A variety of 3-(4-methyl phenyl)-2-substituted amino-3H-quinazolin-4-ones were synthesized by reacting the amino group of 2-hydrazino-3-(4-methyl phenyl)-3H-quinazolin-4-one with a variety of aldehydes and ketones. The starting material 2-hydrazino-3-(4-m

Synthesis and pharmacological investigation of novel 1-alkyl-4-(4- substituted aryl/heteroaryl)-1,2,4-triazolo[4,3-a]quinazolin-5(4H)-ones as a new class of H1-antihistaminic agents

A series of novel 1-alkyl-4-(4-substituted aryl/heteroaryl)-1,2,4- triazolo[4,3-a] quinazolin-5(4H)-ones were synthesized by the cyclization of 2-hydrazino-3-(4-subst. aryl/heteroaryl) quinazolin-4(3H)-one with various carbon donors. The starting material