19062-51-2

Basic information

• Product Name: 2-(bromomethyl)quinazolin-4(1H)-one
• CAS NO: 19062-51-2
• Molecular Formula: C₉H₇BrN₂O
• Molecular Weight: 239.0687
• Mol File: 19062-51-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 353.8°C at 760 mmHg
• Flash Point: 167.8°C
• Density: 1.71g/cm³
• Vapor Pressure: 3.49E-05mmHg at 25°C
• Refractive Index: 1.69
• CAS DataBase Reference: 2-(bromomethyl)quinazolin-4(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(bromomethyl)quinazolin-4(1H)-one(19062-51-2)
• EPA Substance Registry System: 2-(bromomethyl)quinazolin-4(1H)-one(19062-51-2)

Safety Data

• Hazardous Substances Data: 19062-51-2(Hazardous Substances Data)

Usage

Description

2-(bromomethyl)quinazolin-4(1H)-one is a chemical compound that belongs to the quinazolin-4(1H)-one class, featuring a bromomethyl group and a quinazolinone ring structure. 2-(bromomethyl)quinazolin-4(1H)-one is characterized by its potential as a building block in organic synthesis and medicinal chemistry for the creation of various pharmaceutical compounds. The presence of the bromomethyl group on the quinazolinone ring allows for the introduction of other functional groups through nucleophilic substitution reactions, making it a versatile intermediate in the synthesis of bioactive molecules. It holds promise for its own biological activity and plays a significant role in the development of new drugs and the elucidation of structure-activity relationships in medicinal chemistry.

Uses

Used in Organic Synthesis:
2-(bromomethyl)quinazolin-4(1H)-one is used as a building block for the synthesis of various pharmaceutical compounds, leveraging its bromomethyl group to facilitate the introduction of other functional groups via nucleophilic substitution reactions.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-(bromomethyl)quinazolin-4(1H)-one serves as a key intermediate for the development of new drugs, contributing to the understanding of the structure-activity relationship of bioactive molecules.
Used in the Synthesis of Bioactive Molecules:
2-(bromomethyl)quinazolin-4(1H)-one is used as a precursor for the synthesis of bioactive molecules, potentially exhibiting biological activity itself, which is crucial for the advancement of pharmaceutical research and drug discovery.

Upstream product

• 525-76-8 2-methyl-4-oxo-3,1-benzoxazine 
• 118-92-3 anthranilic acid 
• 34637-40-6 2-(hydroxymethyl)quinazolin-4(3H)-one 
• 21721-76-6 2-methoxymethylquinazolin-4(3H)-one 
• 219739-45-4 2-methoxyacetamidobenzonitrile 
• 1885-29-6 anthranilic acid nitrile 
• 129768-71-4 2-(2-Bromo-acetylamino)-benzamide 
• 1769-24-0 2-methyl-4-quinazolone 

Downstream Products

• 21419-63-6 ethyl (4-oxo-3,4-dihydroquinazolin-2-yl)acetate 
• 437998-08-8 2-(aminomethyl)quinazolin-4(3H)-one 
• 30750-23-3 2-(4-oxo-3,4-dihydroquinazolin-2-yl)acetonitrile 
• 1260163-37-8 2-{[5-(4-chlorophenyl)-[1,3,4]thiadiazol-2-ylamino]methyl}-3H-quinazolin-4-one 
• 1260163-33-4 3-(4-oxo-3,4-dihydroquinazolin-2-ylmethyl)-5,5-diphenylimidazolidine-2,4-dione 
• 1260163-54-9 2-{[5-(4-dimethylaminophenyl)-[1,3,4]thiadiazol-2-ylamino]methyl}-3H-quinazolin-4-one 
• 1260163-52-7 2-{[5-(4-methoxyphenyl)-[1,3,4]thiadiazol-2-ylamino]methyl}-3H-quinazolin-4-one 
• 1255216-23-9 C₂₁H₁₅Cl₂N₃O₃S 
• 1255216-14-8 C₂₂H₁₉N₃O₃S 
• 1255216-13-7 C₂₂H₁₉N₃O₄S 
• 1255216-15-9 C₂₁H₁₆ClN₃O₃S 
• 1255216-12-6 C₂₁H₁₇N₃O₃S 
• 1255216-18-2 C₂₃H₂₁N₃O₃S 

Relevant articles and documents

Synthesis and biological evaluation of quinazolin-4(3 H)-one derivatives bearing dithiocarbamate side chain at C2-position as potential antitumor agents

A series of quinazolin-4(3H)-one derivatives bearing dithiocarbamate side chain at the C2-position were synthesized and evaluated for their antiproliferative activities against A549, MCF-7, HeLa, HT29 and HCT-116 cell lines. Most of the synthesized compounds exhibited broad spectrum antitproliferative activity against five cell lines, of which 5c was the most potent against HT29 cell line with an IC50 value of 5.53 μM, inducing a G2/M phase arrest in HT29 cells. Treatment of HT29 cells with 5c resulted in BubR1 phosphorylation and an increase of mitotic index in a time-dependent manner. Furthermore, 5c promoted tubulin polymerization in vitro. These results demonstrate that quinazolin-4(3H)-one derivatives bearing dithiocarbamate side chain at C2-position may be potentially novel antitumor agents targeting tubulin to activate the spindle assembly checkpoint.

Chemical probes to study ADP-ribosylation: Synthesis and biochemical evaluation of inhibitors of the human ADP-ribosyltransferase ARTD3/PARP3

The racemic 3-(4-oxo-3,4-dihydroquinazolin-2-yl)-N-[1-(pyridin-2-yl)ethyl] propanamide, 1, has previously been identified as a potent but unselective inhibitor of diphtheria toxin-like ADP-ribosyltransferase 3 (ARTD3). Herein we describe synthesis and evaluation of 55 compounds in this class. It was found that the stereochemistry is of great importance for both selectivity and potency and that substituents on the phenyl ring resulted in poor solubility. Certain variations at the meso position were tolerated and caused a large shift in the binding pose. Changes to the ethylene linker that connects the quinazolinone to the amide were also investigated but proved detrimental to binding. By combination of synthetic organic chemistry and structure-based design, two selective inhibitors of ARTD3 were discovered.

INHIBITORS OF HEPATITIS C VIRUS RNA-DEPENDENT RNA POLYMERASE, AND COMPOSITIONS AND TREATMENTS USING THE SAME

The invention relates to compounds of the formula (I) and to pharmaceutically acceptable salts, solvates, prodrugs and metabolites thereof, wherein W, Z, R1and R2, are as defined herein. The invention also relates to methods of treating Hepatitis C virus in mammals by administering the compounds of formula (I), and to pharmaceutical compositions for treating such disorders, which contain the compounds of formula (I). The invention also relates to methods of preparing the compounds of formula (I).