13182-47-3

Basic information

• Product Name: 2-Benzoyl-4(3H)-quinazolinone
• Synonyms: 2-Benzoyl-4(3H)-quinazolinone
• CAS NO: 13182-47-3
• Molecular Weight: 250.257
• Mol File: 13182-47-3.mol

Chemical Properties

• CAS DataBase Reference: 2-Benzoyl-4(3H)-quinazolinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Benzoyl-4(3H)-quinazolinone(13182-47-3)
• EPA Substance Registry System: 2-Benzoyl-4(3H)-quinazolinone(13182-47-3)

Safety Data

• Hazardous Substances Data: 13182-47-3(Hazardous Substances Data)

Upstream product

• 122-78-1 phenylacetaldehyde 
• 552-89-6 2-nitro-benzaldehyde 
• 100-42-5 styrene 
• 28144-70-9 anthranilic acid amide 
• 4636-16-2 iodoacetophenone 
• 1074-12-0 phenylglyoxal hydrate 
• 32658-67-6 2-amino-5-iodoanthranilamide 
• 98-86-2 acetophenone 
• 25726-04-9 phenylglyoxylyl chloride 
• 129768-51-0 2-(Phenylglyoxylyl)aminobenzamide 
• 4765-56-4 glycosminine 
• 70-11-1 α-bromoacetophenone 

Downstream Products

• 13182-44-0 2-(α-Hydroxybenzyl)-4(3H)-quinazolinone 

Relevant articles and documents

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.

Electrochemical oxidative synthesis of 2-benzoylquinazolin-4(3: H)-one via C(sp3)-H amination under metal-free conditions

An electrochemically induced C(sp3)-H amination of 2-aminobenzamides with ketones using TBAI as a catalyst was developed, and provided 2-benzoylquinazolin-4(3H)-ones under metal-free conditions. The reaction proceeded using the relatively low-toxicity methanol as the solvent, employed molecular oxygen as the ideal green oxidant in a simple undivided cell, and exhibited high atom economy. The mechanism of this C(sp3)-H amination strategy was concluded to involve generation of an acetophenone radical, and its easy further oxidation to form 2-oxo-2-phenylacetaldehyde.

Ni-catalyzed cascade coupling reactions: synthesis and thermally-activated delayed fluorescence characterization of quinazolinone derivatives

A nickel-catalyzed strategy for the synthesis of 1,3-diaryl-6H-pyrazino[2,1-b]quinazolin-6-one was developed. This method enabled us to access valuable pyrazino-fused quinazolinones with tolerance of many functional groups even at room temperature. The desired pyrazino-fused quinazolinones emit strongly in both solution and solid states. Furthermore, the thermally-activated delayed fluorescence (TADF) of3awas investigated. This study provides an efficient synthetic route for the development of TADF-active pyrazino-fused quinazolinones, thus expanding the application range of this versatile molecular scaffold in optoelectronics.

Benzoylquinazolinone derivatives as new potential antidiabetic agents: α-Glucosidase inhibition, kinetic, and docking studies

Benzoylquinazolinone derivatives 3a–n were synthesized via a simple one-step reaction, and evaluated for in vitro α-glucosidase inhibitory activity. Compounds 3d, 3f–g, 3i, and 3m–n showed more inhibitory activity than standard drug acarbose (IC50 = 750.0 ± 1.5 μM), and among them, compound 3d displayed the highest α-glucosidase inhibitory activity (IC50 = 261.6 ± 0.1 μM). The kinetic analysis of the compound 3d revealed that this compound inhibited α-glucosidase in a competitive manner (Ki = 255 μM). The docking studies were applied to predict binding modes of the synthesized compounds in active site of α-glucosidase.

Discovery of Quinazolin-4(3 H)-ones as NLRP3 Inflammasome Inhibitors: Computational Design, Metal-Free Synthesis, and in Vitro Biological Evaluation

NLRP3 inflammasome is an important therapeutic target for a number of human diseases. Herein, computationally designed series of quinazolin-4(3H)-ones were synthesized using iodine-catalyzed coupling of arylalkynes (or styrenes) with O-aminobenzamides. The key event in this transformation involves the oxidative cleavage of the C-C triple/double bond and the release of formaldehyde. The reaction relies on the C-N bond formation along with the C-C bond cleavage under metal-free conditions. The nitro-substituted quinazolin-4(3H)-one 2k inhibited NLRP3 inflammasome (IC50 5 μM) via the suppression of IL-1β release from ATP-stimulated J774A.1 cells.

Sulfur-Promoted Synthesis of 2-Aroylquinazolin-4(3H)-ones by Oxidative Condensation of Anthranilamide and Acetophenones

A sulfur-promoted three-component reaction of isatoic anhydride, primary aliphatic or aromatic amines, and acetophenones leading to densely substituted 3-substituted 2-aroylquinazolin-4(3H)-ones is reported. The key step involves a cascade reaction of selective oxidation of the methyl group of the acetophenones, followed by a condensation with anthranilamides. The scope of the reaction is applicable to the synthesis of tryptanthrin and various 3-unsubstituted 2-aroylquinazolin-4(3H)-ones. (Figure presented.).

Structure-based drug design: Synthesis and biological evaluation of quinazolin-4-amine derivatives as selective Aurora A kinase inhibitors

Aurora kinases play critical roles in the regulation of the cell cycle and mitotic spindle assembly. Aurora A kinase, a member of the Aurora protein family, is frequently highly expressed in tumors, and selective Aurora A inhibition serves as a significant component of anticancer therapy. However, designing highly selective Aurora A inhibitors is difficult because Aurora A and B share high homology and differ only by three residues in their ATP-binding pockets. Through structure-based drug design, we designed and synthesized a series of novel quinazolin-4-amine derivatives. These derivatives act as selective Aurora A kinase inhibitors by exploiting the structural differences between Aurora A and B. The selectivities of most compounds were improved (the best up to >757-fold) when comparing with the lead compound (3-fold). In vitro biochemical and cellular assays revealed that compound 6 potently inhibited Aurora A kinase and most human tumor cells. Furthermore, compound 6 effectively suppressed carcinoma, such as triple-negative breast cancers (TNBC) in an animal model. Therefore, compound 6 might serve as a promising anticancer drug. Moreover, through molecular dynamic (MD) analysis, we have identified that a salt bridge formed in Aurora B is key contributor for the isoform selectivity of the inhibitor. This salt bridge has not been previously detected in the reported crystal structure of Aurora B. These results might provide a crucial basis for the further development of highly potent inhibitors with high selectivity for Aurora A.

A 2 - benzoyl quinazoline compounds of synthetic method

The invention relates to a method for synthesizing a 2-benzoyl quinazolinone compound: FORMULA. The method comprises the following steps: stirring and hermetically reacting the compound as shown in a formula (II) in an organic solvent in the presence of a palladium catalyst, an oxidant and an alkali to obtain the compound as shown in a formula (I). According to the method provided by the invention, the catalyst, the alkali and the oxidant are properly selected and combined to obtain a target product with high yield, and thus the method has a very high theoretical research value and an application value.

Quinazoline derivative with activity of selectively inhibiting Aurora A kinase, preparation method and application thereof

The invention discloses a quinazoline derivative with activity of selectively inhibiting Aurora A kinase, a preparation method and an application thereof. The invention discloses a compound shown in a formula (I) or (II), or a pharmaceutically-acceptable salt, hydrate, solvate, polymorph, tautomer or prodrug, and simultaneously discloses applications of the compound shown in the formula (I) or (II), or the pharmaceutically-acceptable salt, the hydrate, the solvate, the polymorph, the tautomer or the prodrug in preparing a medicine for inhibiting the Aurora A kinase, and in preparing a medicine for treatment and/or prevention and/or delay and/or auxiliary treatment and/or managing proliferative diseases. The quinazoline derivative disclosed by the invention has better activity and selectivity of inhibiting the Aurora A, simultaneously has obvious inhibiting action for proliferation of tumor cells. The medicine is expected to be combined with the traditional chemotherapeutic drug for use, and has the advantages that the tumor killing effect is enhanced, the recurrence interval is prolonged and the live quality of patients is improved.

Iodine Catalyzed Oxidative Synthesis of Quinazolin-4(3H)-ones and Pyrazolo[4,3-d]pyrimidin-7(6H)-ones via Amination of sp3 C-H Bond

Molecular iodine catalyzed oxidative coupling of 2-aminobenzamides with aryl methyl ketones produced 2-aryl quinazolin-4(3H)-ones. The reaction performed well in the absence of any metal or ligand. The quantity of iodine played a very crucial role in this transformation in order to selectively get 2-aryl quinazolin-4(3H)-ones. The utility of this protocol for synthesis of pyrazolo[4,3-d]pyrimidin-7(6H)-ones including a key intermediate involved in sildenafil synthesis has also been demonstrated.