34637-40-6

Usage

InChI:InChI=1/C9H8N2O2/c12-5-8-10-7-4-2-1-3-6(7)9(13)11-8/h1-4,12H,5H2,(H,10,11,13)

Upstream product

• 3817-05-8 2-(chloromethyl)quinazolin-4(3H)-one 
• 118-92-3 anthranilic acid 
• 28144-70-9 anthranilic acid amide 
• 1885-29-6 anthranilic acid nitrile 
• 219739-45-4 2-methoxyacetamidobenzonitrile 
• 21721-76-6 2-methoxymethylquinazolin-4(3H)-one 
• 129768-44-1 2-(α-Acetoxyacetyl)aminobenzamide 

Downstream Products

• 437998-08-8 2-(aminomethyl)quinazolin-4(3H)-one 
• 21419-63-6 ethyl (4-oxo-3,4-dihydroquinazolin-2-yl)acetate 
• 30750-23-3 2-(4-oxo-3,4-dihydroquinazolin-2-yl)acetonitrile 
• 19062-51-2 2-(bromomethyl)quinazolin-4(3H)-one 

Relevant academic research and scientific papers

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.

A General synthetic procedure for 2-chloromethyl-4(3H)-quinazolinone derivatives and their utilization in the preparation of novel anticancer agents with 4-anilinoquinazoline scaffolds

In our ongoing research on novel anticancer agents with 4-anilinoquinazoline scaffolds, a series of novel 2-chloromethyl-4(3H)- quinazolinones were needed as key intermediates. An improved one-step synthesis of 2-chloromethyl-4(3H)-quinazolinones utilizin

A facile route to quinazolin-4(3H)-ones functionalised at the 2-position

Treatment of 2-methoxyacetamidobenzonitriles or 2- chloroacetamidobenzonitrile with UHP and K2CO3 provides a convenient route to 2-methoxymethyl- or 2-chloromethylquinazolin-4(3H)-ones. In addition, demethylation of 2-methoxymethylqu

Synthesis of chrysogine, a metabolite of Penicillium chrysogenum and some related 2-substituted 4-(3H)-quinazolinones

Syntheses of both enantiomers of chrysogine, 2-(α-hydroxyethyl)-4(3H)-quinazolinone, 1 from 2-ammobenzamide are reported. Thus reaction of 2-aminobenzamide and optically active α-acetoxypropionyl chloride gave 9, which upon saponification and cyclization induced by aqueous sodium carbonate at room temperature gave chrysogine. The enantiomeric purity of 1 was determined by NMR. Inversion of (-)-(S)-1, using the Mitsunobo reaction, gave (+)-(R)-1. Reduction of 2-acetyl-4(3H)-qumazolinone 2 with baker's yeast gave the S-enantiomer of 1. The cyclization method used could be extended and a number of 2-(a-hydroxy)alkyl-4-(3H)-quinazolinones are also reported.