66679-74-1

Basic information

• Product Name: 2,4(1H,3H)-Quinazolinedione, 3-(4-chlorophenyl)-, 2-hydrazone
• CAS NO: 66679-74-1
• Molecular Formula: C14H11ClN4O
• Molecular Weight: 286.721
• Mol File: 66679-74-1.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 2,4(1H,3H)-Quinazolinedione, 3-(4-chlorophenyl)-, 2-hydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4(1H,3H)-Quinazolinedione, 3-(4-chlorophenyl)-, 2-hydrazone(66679-74-1)
• EPA Substance Registry System: 2,4(1H,3H)-Quinazolinedione, 3-(4-chlorophenyl)-, 2-hydrazone(66679-74-1)

Safety Data

• Hazardous Substances Data: 66679-74-1(Hazardous Substances Data)

Upstream product

• 1031-97-6 2-methylsulfanyl-3-(4-chlorophenyl)-3H-quinazolin-4-one 
• 1028-40-6 3-(4-chlorophenyl)-2-thioxo-2,3-dihydro-1H-quinazolin-4-one 
• 1028-40-6 2-sulfhydryl-3-(4-chlorophenyl)-quinazolin-4(3H)-one 
• 89913-67-7 4-chlorophenyldithiocarbamate sodium salt 
• 705-69-1 N-(4-chlorophenyl)-S-methyldithiocarbamate 
• 118-92-3 anthranilic acid 
• 2131-55-7 4-Chlorophenyl isothiocyanate 
• 106-47-8 4-chloro-aniline 

Downstream Products

• 85772-64-1 1-chloromethyl-4-(4-chlorophenyl)-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one 
• 1146963-37-2 4-(4-chlorophenyl)-1-o-tolyl-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one 
• 77437-34-4 3-(4-Chloro-phenyl)-2-{N'-[4-(4-chloro-phenyl)-3-phenyl-3H-thiazol-(2Z)-ylidene]-hydrazino}-3H-quinazolin-4-one 
• 77437-35-5 2-{N'-[3-(4-Bromo-phenyl)-4-phenyl-3H-thiazol-(2Z)-ylidene]-hydrazino}-3-(4-chloro-phenyl)-3H-quinazolin-4-one 
• 96936-39-9 3-(4-Chloro-phenyl)-2-(3-methyl-5-oxo-2,5-dihydro-pyrazol-1-yl)-3H-quinazolin-4-one 
• 85772-62-9 1-propyl-4-(4-chlorophenyl)-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one 
• 68357-61-9 1-methyl-4-(4-chlorophenyl)-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one 
• 95241-44-4 3-amino-2-[(4-chlorophenyl)amino]-4(3H)-quinazolinone 
• 85773-11-1 Pentanoic acid N'-[3-(4-chloro-phenyl)-4-oxo-3,4-dihydro-quinazolin-2-yl]-hydrazide 
• 132331-13-6 3-p-chlorophenyl-2-<1-ethoxycarbonyl-1-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)hydrazono-2-propylidene>-hydrazino-4(3H)-quinazolinone 
• 132331-17-0 3-p-chlorophenyl-2-<4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)hydrazono-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl>-4(3H)-quinazolinone 
• 132331-21-6 3-p-chlorophenyl-2-<4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-azo-3,5-dimethyl-1H-pyrazol-1-yl>-4(3H)-quinazolinone 
• 85773-29-1 3-[4-(4-Chloro-phenyl)-5-oxo-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinazolin-1-yl]-propionic acid ethyl ester 
• 85773-09-7 Butyric acid N'-[3-(4-chloro-phenyl)-4-oxo-3,4-dihydro-quinazolin-2-yl]-hydrazide 

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.

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.

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.