1152-07-4

Usage

Uses

Used in Oncology:
2-(4-methoxyphenyl)-1H-quinazolin-4-one is used as a potential drug candidate for the treatment of cancer due to its anti-tumor effects. It has shown promise in inhibiting tumor growth and progression, making it a valuable compound in the field of oncology.
Used in Epigenetic Research:
2-(4-methoxyphenyl)-1H-quinazolin-4-one is used as an inhibitor of histone methyltransferase, an enzyme involved in epigenetic regulation. Its potential role in modulating epigenetic processes makes it a valuable tool in the study of gene expression and regulation, with potential applications in the development of targeted therapies for various diseases.
Used in Drug Development:
2-(4-methoxyphenyl)-1H-quinazolin-4-one is used as a lead compound in the development of new drugs, particularly for the treatment of cancer. Its bioactivity and potential therapeutic applications make it a promising candidate for further research and development in the pharmaceutical industry.

Upstream product

• 55390-89-1 2-(4-Methoxybenzamido)benzamide 
• 28005-57-4 N-(2-ethoxycarbonylphenyl)-4-methoxythiobenzamide 
• 85094-68-4 N-(2-cyclohexylcarbamoylphenyl)-4-methoxythiobenzamide 
• 88185-00-6 2-(4-methoxyphenyl)-3,4-dihydro-5H-1,3,4-benzotriazepin-5-one 
• 123-11-5 4-methoxy-benzaldehyde 
• 28144-70-9 anthranilic acid amide 
• 100-09-4 4-methoxybenzoic acid 
• 175794-24-8 4-anthraniloylhydrazono-2,6-di-tert-butyl-2,5-cyclohexadienone 
• 10345-77-4 2-nitro-N,N-diethylbenzamide 
• 874-90-8 4-methoxybenzonitrile 
• 67854-76-6 2-(4-Methoxy-phenyl)-1,2,3,4-tetrahydro-chinazolin 
• 61666-75-9 2-(4-metoxyphenyl)benzo[d][1,3]dithiole 
• 107920-18-3 2-(4-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one 
• 3424-93-9 4-methoxyphenylacetamide 

Downstream Products

• 55391-00-9 2-(p-methoxyphenyl)-4-chloroquinazoline 
• 1382529-60-3 C₂₂H₁₈N₂OS 
• 1520087-41-5 2-(4-methoxyphenyl)-4-(p-tolyl)quinazoline 
• 1520087-43-7 4-(4-chlorophenyl)-2-(4-methoxyphenyl)quinazoline 
• 84570-80-9 2-(4-methoxylphenyl)-4-phenylquinazoline 

Relevant academic research and scientific papers

Metal-free synthesis of quinazolinones without any additives in water

Here we report that an excess amount of aldehyde, in particular, aliphatic aldehyde, without any additives, efficiently facilitates the oxidation of aminal intermediates to quinazolinones in pure water.

An efficient an one-pot method for synthesis of 2-Aryl-(3H)-4-quinazolinones derivatives catalyzed by SSA

A mixture of 2-amino benzamide with aromatic aldehyds in the presence of SSA under solvent-free condition were converted to quinazolinones with good yields.

One pot synthesis of 4(3H)-quinazolinones

Anthranilamides undergo cyclocondensation with aldehydes in presence of iodine in a single-pot reaction to afford 2-substituted 4(3H)-quinazolinones in moderate to excellent yield (40-95%). 2,3-Substituted 4(3H)-quinazolinones are synthesized in moderate to good yield by three-component condensation of isotoic anhydride, amine, and aldehyde in presence of iodine.

N^N^O hydrazone capped pincer type palladium complex catalysed construction of quinazolinones from alcohols

New Pincer type Pd(II) complex [Pd(NNO)(PPh3)] (1) prompted synthesis of quinazolinones via dehydrogenative coupling of readily accessible alcohols, and o-aminobenzamide is described. A diverse range of quinazolinones has been synthesized efficiently with good to excellent yields employing low catalyst loading (0.5 mol%) under the aerobic condition without any additives/oxidants. A plausible mechanism for the construction of quinazolinones has been proposed via cyclic aminal intermediate. Large-scale synthesis attests to the productiveness of the current strategy.

A bagasse-supported magnetic manganese dioxide nanoparticle: applications in the selective aerobic oxidation of alcohols and one-pot tandem oxidative synthesis of quinazolinones

Magnetic manganese dioxide nanoparticles (MnO2-Fe3O4) were coated on sugarcane bagasse as a sugar industrial waste and bio-support (MnO2-Fe3O4@bagasse) via an in situ reduction strategy, in which potassium permanganate was used as the precursor of MnO2 and sugarcane bagasse as a bio-support and reducing agent of KMnO4. The synthesized bio-based catalyst was characterized by X-ray diffraction, thermogravimetric analysis, inductively coupled plasma optical emission spectroscopy, scanning electron microscopy, energy dispersive spectroscopy, Brunauer–Emmett–Teller surface area analysis, and vibrating sample magnetometer analysis. The catalyst was successfully utilized in the selective aerobic oxidation of primary and secondary benzylic alcohols to their corresponding carbonyl compounds and one-pot tandem oxidative synthesis of 2-(substituted)quinazoline-4(3H)-ones from the o-aminobenzamide and aromatic alcohols in the absence of oxidizing reagent or initiator. Graphical abstract: [Figure not available: see fulltext.]

Synthesis, in vitro cytotoxic, anti-Mycobacterium tuberculosis and molecular docking studies of 4-pyridylamino- and 4-(ethynylpyridine)quinazolines

A series of 4-(pyridylamino)- and 4-(ethynylpyridine)quinazolines were successfully prepared via Sonogashira cross-coupling and dechloroamination reactions on the C(4)-Cl position of the requisite 2-(p-phenyl)-4-chloroquinazolines. The prepared compounds were characterized by means of 1H- and 13C-NMR, FT-IR and mass spectrometry techniques. The structure of 2-(4-chlorophenyl)-4-(2-(pyridin-4-yl) ethynyl) quinazoline from the 4-(ethynylpyridine) series was confirmed by single crystal X-ray analysis which indicates monoclinic crystal system and P21/c space group. Compounds from the 4-chloro-, 4-(pyridylamino)- and 4-(ethynylpyridine)-quinazoline series were evaluated for anti-Mycobacterium tuberculosis (Mtb) properties in vitro employing rifampicin as a reference drug. The results from the Alamar Blue assay (Mtb H37Rv strain) revealed promising MIC90 ranging from 125 μM. The cytotoxicity of the synthesised compounds was tested against the Raw 264.7 microphage cell line at a maximum concentration of 50 μM. The possible mode of interaction against the Mtb was theoretically explained through molecular 3ZXR protein and the more prominent hydrogen bond is observed between the nitrogen of the pyridine ring moiety of the 5 and 6 series with OH group of SER280. Also, a metal coordination between the methoxy benzene moiety of compound 6e and Mg2+ is also observed, explaining the SAR of these compounds to MtGS.

A magnetically retrievable copper ionic liquid nanocatalyst for cyclooxidative synthesis of 2-phenylquinazolin-4(3: H)-ones

In the present work, we report the design and fabrication of a copper-containing ionic liquid supported magnetic nanocatalyst via a convenient and straightforward synthetic approach for the formation of 2-phenylquinazolin-4(3H)-ones using o-aminobenzamide and benzaldehydes as the reaction partners. The successful formation and properties of the as-prepared catalyst have been thoroughly investigated using diverse physico-chemical techniques including FT-IR, XRD, FE-SEM, TEM, ICP, VSM, BET and TGA. Using this nanocatalytic system, a variety of 2-phenylquinazolin-4(3H)-ones are synthesized in excellent yields with operational ease and short reaction times in an environmentally preferable solvent under open air and without using any external oxidizing agent. Besides, the catalyst possessed facile magnetic recoverability and remarkable reusability for six consecutive runs without any appreciable decrease in the catalytic efficiency.

Metal-free catalyst for the visible-light-induced photocatalytic synthesis of quinazolinones

In the present work, we have developed a novel and environmentally friendly method for the synthesis of quinazolinones using fluorescein as a photocatalyst via a condensation reaction of o-aminobenzamides and aldehydes under visible light irradiation. In this protocol, neither toxic oxidants nor transition-metal catalysts were needed, and a series of quinazolinones could be obtained in high efficiencies. In addition, this reaction can be extended to gram levels and has a large potential of wide application in future industrialization.

KOtBu-BF3.OEt2 mediated synthesis of quinazolin-4(3H)-ones from 2-substituted amides with nitriles and aldehydes

KOtBu-BF3.OEt2 mediated synthesis of quinazolin-4(3H)-ones from 2-substituted amides with nitriles and aldehydes have been developed. In this protocol, a variety of nitriles as well as aldehydes react with 2-substituted benzamides to corresponding quinazolin-4(3H)-ones products in good to moderate yields, via the cleavage of C-X and C-N bonds and the formation of double C-N bonds simultaneously, in presence of potassium tert-butoxide.

Visible-light-mediated organoboron-catalysed metal-free dehydrogenation of N-heterocycles using molecular oxygen

The surge of photocatalytic transformation not only provides unprecedented synthetic methods, but also triggers the enthusiasm for more sustainable photocatalysts. On the other hand, oxygen is an ideal oxidant in terms of atom economy and environmental friendliness. However, the poor reactivity of oxygen at the ground state makes its utilization challenging. Herein, a visible-light-induced oxidative dehydrogenative process is disclosed, which uses an organoboron compound as the photocatalyst and molecular oxygen as the sole oxidant.Viathis approach, an array of N-heterocycles have been accessed under metal-free mild conditions, in good to excellent yields.