18818-41-2

Usage

Core structure

Quinazolinone core.

Derivative

It is a derivative of quinazoline.

Biological activities

Anti-tumor, anti-inflammatory, and anti-microbial properties.

Potential use

In cancer therapy.

Promising results

Inhibiting the growth of certain cancer cell lines.

Anti-inflammatory effects

Suppressing the production of inflammatory mediators.

Versatile compound

Potential applications in medicine and pharmacology.

Upstream product

• 13324-79-3 2,3-dihydro-2-(4-methylphenyl)quinazolin-4(1H)-one 
• 52910-88-0 N-(2-carbamoylphenyl)-4-methylbenzamide 
• 104-87-0 4-methyl-benzaldehyde 
• 28144-70-9 anthranilic acid amide 
• 82255-95-6 [1-Phenylamino-1-p-tolyl-meth-(E)-ylidene]-carbamic acid ethyl ester 
• 88184-99-0 2-(p-methylphenyl)-3,4-dihydro-5H-1,3,4-benzotriazepin-5-one 
• 827-71-4 4-methyl-benzimidic acid ethyl ester 
• 118-92-3 anthranilic acid 
• 99-94-5 p-Toluic acid 
• 63002-95-9 3-amino-2-(4-methylphenyl)quinazolin-4(3H)-one 
• 153172-69-1 N-(2-cyanophenyl)-4-methylbenzamide 
• 1486-28-8 diphenyl(methyl)phosphine 
• 287976-89-0 N-(4-methylbenzoyl)-2-azidobenzamide 
• 10345-77-4 2-nitro-N,N-diethylbenzamide 

Downstream Products

• 65772-26-1 3-morpholin-4-ylmethyl-2-p-tolyl-3H-quinazolin-4-one 
• 59490-96-9 4-chloro-2-(p-tolyl)quinazoline 
• 1233224-89-9 3-[1-hydroxy-1-(4-nitrophenyl)methyl]-5-(4-methylphenyl)[1,2,4]triazolo[4,3-c]quinazoline 
• 1233224-85-5 C₂₃H₁₈N₄O 
• 1382529-52-3 4-(4-fluorophenylsulfanyl)-2-p-tolylquinazoline 
• 1382529-53-4 4-(4-chlorophenylsulfanyl)-2-p-tolylquinazoline 
• 1382529-54-5 4-(2-chlorophenylsulfanyl)-2-p-tolylquinazoline 
• 1382529-55-6 4-benzylsulfanyl-2-p-tolylquinazoline 
• 1382529-50-1 2-p-tolyl-4-p-tolylsulfanylquinazoline 
• 1382529-51-2 4-phenylsulfanyl-2-p-tolylquinazoline 
• 1537879-15-4 3-methyl-5,6-di-p-tolyl-8H-isoquinolino[1,2-b]quinazolin-8-one 

Relevant academic research and scientific papers

Access to 2-Arylquinazolin-4(3H)-ones through Intramolecular Oxidative C(sp3)?H/N?H Cross-Coupling Mediated by I2/DMSO

A novel approach for the synthesis of 2-arylquinazolin-4(3H)-ones was developed. A series of title compounds were obtained with good functional group tolerance and good yields by I2/DMSO-mediated intramolecular oxidative cross-coupling of 2-(benzylamino)benzamides to form C=N double bonds. This method was applicable for gram-scale synthesis. A proposed reaction pathway based on some control experiments was also provided.

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.

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.

Improved, gram-scale synthesis of sildenafil in water using arylacetic acid as the acyl source in the pyrazolo[4,3-d]pyrimidin-7-one ring formation

An improved, gram-scale synthesis of the blockbuster drug sildenafil, used for the treatment of male erectile dysfunction, has been developed. Unlike the previous literature, the current method demonstrates the use of arylacetic acid as an acyl source, a cheap oxidant K2S2O8, and water as the reaction medium in the key step of pyrrazolo[4,3-d]pyrimidin-7-one ring formation. As well as being a green and benign approach, the current method reduces the cost by half compared to our previous strategy. In addition, the general relevance of the method has been demonstrated in the synthesis of a variety of quinazolinone and benzothiazole derivatives with excellent functional group tolerance.

α-Keto Acids as Triggers and Partners for the Synthesis of Quinazolinones, Quinoxalinones, Benzooxazinones, and Benzothiazoles in Water

A general and efficient method for the synthesis of quinazolinones, quinoxalinones, benzooxazinones, and benzothiazoles from the reactions of α-keto acids with 2-aminobenzamides, benzene-1,2-diamines, 2-aminophenols, and 2-aminobenzenethiols, respectively, is described. The reactions were conducted under catalyst-free conditions, using water as the sole solvent with no additive required, and successfully applied to the synthesis of sildenafil. More importantly, these reactions can be conducted on a mass scale, and the products can be easily purified through filtration and washing with ethanol (or crystallized).

Catalyst-free synthesis of quinazolinones by oxidative cyclization under visible light in the absence of additives

A general metal-free oxidative cyclization route was developed to synthesize quinazolinones under visible light. A series of substituted 2-aminobenzamides were reacted with aldehydes or ketones to produce the desired quinazolinones in good yields. Most importantly, the reaction did not require excess oxidant or high temperatures.

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.

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.

Method for synthesizing quinazolinone compound through visible light induction

The method is mild in reaction condition, simple and convenient in post-treatment operation, free of additional additives, high I in reaction efficiency, wide II in substrate adaptability, high in product purity, green and environment-friendly, and the method has III the advantages of mild reaction conditions, no need of additional additives, high reaction efficiency, wide substrate adaptability.

Discovery of Novel Dual-Target Inhibitor of Bromodomain-Containing Protein 4/Casein Kinase 2 Inducing Apoptosis and Autophagy-Associated Cell Death for Triple-Negative Breast Cancer Therapy

Bromodomain-containing protein 4 (BRD4) is an attractive epigenetic target in human cancers. Inhibiting the phosphorylation of BRD4 by casein kinase 2 (CK2) is a potential strategy to overcome drug resistance in cancer therapy. The present study describes the synthesis of multiple BRD4–CK2 dual inhibitors based on rational drug design, structure–activity relationship, and in vitro and in vivo evaluations, and 44e was identified to possess potent and balanced activities against BRD4 (IC50 = 180 nM) and CK2 (IC50 = 230 nM). In vitro experiments show that 44e could inhibit the proliferation and induce apoptosis and autophagy-associated cell death of MDA-MB-231 and MDA-MB-468 cells. In two in vivo xenograft mouse models, 44e displays potent anticancer activity without obvious toxicities. Taken together, we successfully synthesized the first highly effective BRD4–CK2 dual inhibitor, which is expected to be an attractive therapeutic strategy for triple-negative breast cancer (TNBC).