19062-51-2

Usage

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

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

Downstream Products

• 1255216-19-3 C₂₄H₂₃N₃O₃S 
• 1255216-22-8 C₂₄H₂₂ClN₃O₃S 
• 1255216-20-6 C₂₅H₂₅N₃O₄S 
• 1255216-21-7 C₂₅H₂₅N₃O₃S 
• 1255216-24-0 C₂₂H₁₉N₃O₃S 
• 1255216-16-0 C₂₂H₁₉N₃O₃S 
• 1255216-17-1 C₂₃H₂₁N₃O₄S 
• 1255216-18-2 C₂₃H₂₁N₃O₃S 
• 1255216-12-6 C₂₁H₁₇N₃O₃S 
• 1255216-15-9 C₂₁H₁₆ClN₃O₃S 
• 1255216-13-7 C₂₂H₁₉N₃O₄S 
• 1255216-14-8 C₂₂H₁₉N₃O₃S 
• 1255216-23-9 C₂₁H₁₅Cl₂N₃O₃S 
• 1260163-37-8 2-{[5-(4-chlorophenyl)-[1,3,4]thiadiazol-2-ylamino]methyl}-3H-quinazolin-4-one 

Relevant academic research and scientific papers

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.

Microwave assisted synthesis of pyridin-1-ium salt of 6-nitroquinazolin-4-one and its 6-amino analog under ultrasonic irradiation

The new compounds of quinazolin-4-one derivative i.e., 2-methyl-6-nitroquinazolin-4-one substituted pyridin-1-ium salt at methyl group and its 6-amino analog have been synthesized. Microwave irradiation of solution of 2-bromomethyl-6- nitroquinazolin-4-one and pyridine in acetonitrile for 3 min afforded 1-[(6-nitroquinazolin-4-one-2-yl)methyl]pyridin-1-ium bromide; and nitro reduction of the product with iron in ethanol/acetic acid/water under ultrasonic irradiation afforded 1-[(6-aminoquinazolin-4-one-2-yl)methyl]pyridin-1-ium bromide. The structure of the synthesized compounds were confirmed on the basis of FT-IR, 1H NMR and 13C NMR data.

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 1 and to pharmaceutically acceptable salts, solvates, prodrugs and metabolites thereof, wherein W, Z, R1 and R2, are as defined herein. The invention also relates to methods of treating Hepatitis C virus in mammals by administering the compounds of formula 1, and to pharmaceutical compositions for treating such disorders, which contain the compounds of formula 1. The invention also relates to methods of preparing the compounds of formula 1.

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).

Synthesis and in vitro antifungal activity of some N,N-disubstituted dithiocarbamic acid esters derived from 2-methylquinazolinones

A series of 2-[(N,N-disubstituted thiocarbamoylthio)methyl]quinazolinones 9a-g; 10a; 10d; 11a-d and 12a were synthesized and evaluated for potential antifungal activity against a variety of fungal species. The synthesis of the target compounds was achieved by reaction of the potassium salts of disubstituted dithiocarbamic acids 8a-g and the respective 2-bromomethyl-4(3H)-quinazolinone 4 or 3-aryl-2- chloromethyl-4(3H)-quinazolinones 5-7. The dithiocarbamic acid derivatives were synthesized in a one step reaction from the appropriate amine, alcoholic potassium hydroxide solution and carbon disulfide. TLC and elemental analyses ascertained the purity of the synthesized compounds and their structures were confirmed by IR and 1H-NMR spectroscopy, 2-Methyl-4(3H)-quinazolinone 2, the precursor of the 2-bromomethyl intermediate 4, was selected as representative example for detailed spectroscopic investigations, including 300 MHz 1H- and 13CNMR in addition to HH COSY; APT and 1H13C HETCOR spectra, with the aim of establishing correct assignment of the spectral data of related compounds. The synthesized disubstituted dithiocarbamates 9a-g; 10a,d; 11a-d and 12a as well as tolnaftate and clotrimazole, as reference drugs, were tested in vitro at 2 and 5% concentrations against 23 pathogenic fungi. The study revealed that compound 9a exhibited broad spectrum inhibitory activity that is superior or comparable to that of the reference drugs against the tested fungal isolates. Selective fungistatic activity against Candida species was elicited by compound 9e and against Microsporum species as well as Trichophyton mentagrophytes was also observed for compound 9g. As a general pattern it might be postulated that some of the synthesized dithiocarbamate derivatives showed broad spectrum antifungal activity as compared with tolnaftate, the clinically used thiocarbamate compound, and also exhibited comparable activity to clotrimazole against Candida species and F. Solani.

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.