6958-39-0

Basic information

• Product Name: 6,7-DICHLOROQUINAZOLIN-4(3H)-ONE
• Synonyms: 6,7-DICHLOROQUINAZOLIN-4(3H)-ONE;6,7-Dichloro-3H-quinazolin-4-one
• CAS NO: 6958-39-0
• Molecular Formula: C₈H₄Cl₂N₂O
• Molecular Weight: 215.03616
• Mol File: 6958-39-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 625.6°C at 760 mmHg
• Flash Point: 332.2°C
• Appearance: /
• Density: 1.44g/cm³
• Vapor Pressure: 1.44E-15mmHg at 25°C
• Refractive Index: 1.714
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 6,7-DICHLOROQUINAZOLIN-4(3H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7-DICHLOROQUINAZOLIN-4(3H)-ONE(6958-39-0)
• EPA Substance Registry System: 6,7-DICHLOROQUINAZOLIN-4(3H)-ONE(6958-39-0)

Safety Data

• Hazardous Substances Data: 6958-39-0(Hazardous Substances Data)

Usage

General Description

6,7-Dichloroquinazolin-4(3H)-one, also known as DCQ, is a chemical compound with a molecular formula C8H4Cl2N2O. It is a heterocyclic organic compound consisting of a quinazoline ring with two chlorine atoms attached at positions 6 and 7. DCQ has been studied for its potential pharmacological and biological activities, particularly as an antiparasitic agent. It has shown promise in inhibiting the growth and survival of parasites such as Plasmodium falciparum, the causative agent of malaria, and can also be used as a tool for studying biological pathways and chemical biology. Additionally, DCQ has demonstrated potential as a starting material for the synthesis of other biologically active molecules due to its unique chemical structure.

InChI:InChI=1/C19H11N5O2/c20-10-12-4-6-13(7-5-12)16-9-18(23-19(22)17(16)11-21)14-2-1-3-15(8-14)24(25)26/h1-9H,(H2,22,23)

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Relevant articles and documents

Structure-guided optimization and mechanistic study of a class of quinazolinone-threonine hybrids as antibacterial ThrRS inhibitors

Aminoacyl-tRNA synthetases (aaRSs) are an attractive class of antibacterial drug targets due to their essential roles in protein translation. While most traditional aaRS inhibitors target the binding pockets of substrate amino acids and/or ATP, we recently developed a class of novel tRNA-amino acid dual-site inhibitors including inhibitor 3 ((2S,3R)-2-amino-N-((E)-4-(6,7-dichloro-4-oxoquinazolin-3(4H)-yl)but-2-en-1-yl)-3-hydroxybutanamide) against threonyl-tRNA synthetase (ThrRS). Here, the binding modes and structure-activity relationships (SARs) of these inhibitors were analyzed by the crystal structures of Salmonella enterica ThrRS (SeThrRS) in complex with three of them. Based on the cocrystal structures, twelve quinazolinone-threonine hybrids were designed and synthesized, and their affinities, enzymatic inhibitory activities, and cellular potencies were evaluated. The best derivative 8g achieved a Kd value of 0.40 μM, an IC50 value of 0.50 μM against SeThrRS and MIC values of 16–32 μg/mL against the tested bacterial strains. The cocrystal structure of the SeThrRS-8g complex revealed that 8g induced a bended conformation for Met332 by forming hydrophobic interactions, which better mimicked the binding of tRNAThr to ThrRS. Moreover, the inhibitory potency of 8g was less impaired than a reported ATP competitive inhibitor at high concentrations of ATP, supporting our hypothesis that tRNA site inhibitors are likely superior to ATP site inhibitors in vivo, where ATP typically reaches millimolar concentrations.