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

• 28005-57-4 N-(2-ethoxycarbonylphenyl)-4-methoxythiobenzamide 
• 28144-70-9 anthranilic acid amide 
• 100-09-4 4-methoxybenzoic acid 
• 85094-63-9 2-(4-methoxyphenyl)-4H-3,1-benzothiazin-4-one 
• 55390-99-3 3-amino-2-(4-methoxyphenyl)-4(3H)-quinazolinone 
• 118-48-9 isatoic anhydride 
• 123-11-5 4-methoxy-benzaldehyde 
• 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 
• 18600-55-0 2-(4-methoxyphenyl)-4H-3,1-benzoxazin-4-one 
• 24588-72-5 2-(4-methoxyphenyl)-1,3-dithiane 
• 61666-75-9 2-(4-metoxyphenyl)benzo[d][1,3]dithiole 
• 107920-18-3 2-(4-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one 

Downstream Products

• 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.]

Palladium-catalyzed one-pot synthesis of 2-substituted quinazolin-4(3H)-ones fromo-nitrobenzamide and alcohols

Palladium-catalyzed 2-substituted quinazolin-4(3H)-one formation from readily availableo-nitrobenzamides and alcohols using hydrogen transfer is described. Various quinazolin-4(3H)-ones were obtained in good to high yields. The cascade reaction including

Ammonium formate-Pd/C as a new reducing system for 1,2,4-oxadiazoles. Synthesis of guanidine derivatives and reductive rearrangement to quinazolin-4-ones with potential anti-diabetic activity

1,2,4-Oxadiazole is a heterocycle with wide reactivity and many useful applications. The reactive O-N bond is usually reduced using molecular hydrogen to obtain amidine derivatives. NH4 CO2 H-Pd/C is here demonstrated as a new system for the O-N reduction, allowing us to obtain differently substituted acylamidine, acylguanidine and diacylguanidine derivatives. The proposed system is also effective for the achievement of a reductive rearrangement of 5-(2′-aminophenyl)-1,2,4-oxadiazoles into 1-alkylquinazolin-4(1H)-ones. The alkaloid glycosine was also obtained with this method. The obtained compounds were preliminarily tested for their biological activity in terms of their cytotoxicity, induced oxidative stress, α-glucosidase and DPP4 inhibition, showing potential application as anti-diabetics.

Copper-Catalyzed One-Pot Synthesis of Quinazolinones from 2-Nitrobenzaldehydes with Aldehydes: Application toward the Synthesis of Natural Products

A novel, efficient, and atom-economical approach for the construction of quinazolinones from 2-nitrobenzaldehydes has been unveiled via copper-catalyzed nitrile formation, hydrolysis, and reduction in one pot for the first time. In this reaction, urea is used as a source of nitrogen for nitrile formation, hydrazine hydrate is used for both the reduction of the nitro group and the hydrolysis of nitrile, and atmospheric oxygen is used as the sole oxidant. The method portrays a wide substrate scope with good functional group tolerances. Moreover, this method was applied for the synthesis of schizocommunin, tryptanthrin, phaitanthrin-A, phaitanthrin-B, and 8H-quinazolino[4,3-b]quinazolin-8-one.

Regioselective Synthesis of 2° Amides Using Visible-Light-Induced Photoredox-Catalyzed Nonaqueous Oxidative C-N Cleavage of N, N-Dibenzylanilines

A visible-light-driven photoredox-catalyzed nonaqueous oxidative C-N cleavage of N,N-dibenzylanilines to 2° amides is reported. Further, we have applied this protocol on 2-(dibenzylamino)benzamide to afford quinazolinones with (NH4)2S2O8 as an additive. Mechanistic studies imply that the reaction might undergo in situ generation of α-amino radical to imine by C-N bond cleavage followed by the addition of superoxide ion to form amides.

An efficient transition-metal-free route to quinazolin-4(3H)-onesvia2-aminobenzamides and thiols

An efficient approach to quinazolin-4(3H)-ones was developed by a one-pot intermolecular annulation reaction ofo-amino benzamides and thiols. This method has the features of good functional group tolerance, being transition metal and external oxidant free, and easy operation. Varieties of 2-aryl (heteroaryl) quinazolin-4(3H)-one, 2-phenyl-pyrido[2,3-d]pyrimidin-4(3H)-one and 3-phenyl-2H-1,2,4-benzo thiadiazine-1,1-dioxide derivatives were obtained with a yield of up to 98%. The control experiment revealed that the thiol substrate could promote the dehydroaromatization step.