86662-57-9

Basic information

• Product Name: 3-ETHYL-2-HYDRAZINOQUINAZOLIN-4(3H)-ONE
• Synonyms: 4(3H)-Quinazolinone,3-ethyl-2-hydrazinyl-;3-Ethyl-2-hydrazinyl-4(3H)-quinazolinone
• CAS NO: 86662-57-9
• Molecular Formula: C₁₀H₁₂N₄O
• Molecular Weight: 204.23
• Mol File: 86662-57-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 375.1°C at 760 mmHg
• Flash Point: 180.6°C
• Appearance: /
• Density: 1.36g/cm³
• Vapor Pressure: 7.99E-06mmHg at 25°C
• Refractive Index: 1.672
• CAS DataBase Reference: 3-ETHYL-2-HYDRAZINOQUINAZOLIN-4(3H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ETHYL-2-HYDRAZINOQUINAZOLIN-4(3H)-ONE(86662-57-9)
• EPA Substance Registry System: 3-ETHYL-2-HYDRAZINOQUINAZOLIN-4(3H)-ONE(86662-57-9)

Safety Data

• Hazardous Substances Data: 86662-57-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H12N4O/c1-2-14-9(15)7-5-3-4-6-8(7)12-10(14)13-11/h3-6H,2,11H2,1H3,(H,12,13)

Upstream product

• 126135-06-6 3-ethyl-2-(methylthio)quinazolin-4(3H)-one 
• 13906-08-6 3‐ethyl‐2‐thioxo‐2,3‐dihydroquinazolin‐4(1H)‐one 
• 118-92-3 anthranilic acid 
• 13906-08-6 3-ethyl-2-mercapto-4(3H)-quinazolinone 

Downstream Products

• 19062-39-6 3-amino-2-hydrazinoquinazolin-4(3H)-one 
• 1649985-41-0 3-ethyl-2-(5-phenyl-3-(p-tolyl)-4,5-dihydropyrazol-1-yl)-3H-quinazolin-4-one 
• 1649985-42-1 2-[5-(4-chlorophenyl)-3-(p-tolyl)-4,5-dihydropyrazol-1-yl]-3-ethyl-3H-quinazolin-4-one 
• 1649985-43-2 2-(3,5-di-(p-tolyl)-4,5-dihydropyrazol-1-yl)-3-ethyl-3H-quinazolin-4-one 
• 1649985-44-3 2-[5-(4-bromophenyl)-3-(p-tolyl)-4,5-dihydro-pyrazol-1-yl]-3-ethyl-3H-quinazolin-4-one 
• 1649985-45-4 2-[3-(4-chlorophenyl)-5-phenyl-4,5-dihydro-pyrazol-1-yl]-3-ethyl-3H-quinazolin-4-one 
• 1649985-46-5 2-[3,5-bis-(4-chlorophenyl)-4,5-dihydro-pyrazol-1-yl]-3-ethyl-3H-quinazolin-4-one 
• 1649985-48-7 2-[5-(4-bromophenyl)-3-(4-chloro-phenyl)-4,5-dihydropyrazol-1-yl]-3-ethyl-3H-quinazolin-4-one 
• 109192-45-2 1-(4-chlorophenyl)-4-ethyl<1,2,4>triazolo<4,3-a>quinazolin-5-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.

Identification of a New Heterocyclic Scaffold for Inhibitors of the Polo-Box Domain of Polo-like Kinase 1

As a mitotic-specific target widely deregulated in various human cancers, polo-like kinase 1 (Plk1) has been extensively explored for anticancer activity and drug discovery. Although multiple catalytic domain inhibitors were tested in preclinical and clinical studies, their efficacies are limited by dose-limiting cytotoxicity, mainly from off-target cross reactivity. The C-terminal noncatalytic polo-box domain (PBD) of Plk1 has emerged as an attractive target for generating new protein-protein interaction inhibitors. Here, we identified a 1-thioxo-2,4-dihydro-[1,2,4]triazolo[4,3-a]quinazolin-5(1H)-one scaffold that efficiently inhibits Plk1 PBD but not its related Plk2 and Plk3 PBDs. Structure-activity relationship studies led to multiple inhibitors having ≥10-fold higher inhibitory activity than the previously characterized Plk1 PBD-specific phosphopeptide, PLHSpT (Kd ～450 nM). In addition, S-methyl prodrugs effectively inhibited mitotic progression and cell proliferation and their metabolic stability was determined. These data describe a novel class of small-molecule inhibitors that offer a promising avenue for future drug discovery against Plk1-addicted cancers.

Synthesis of [1,2,4]triazoloquinazolinones and imidazoquinazolinones

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