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 
• 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 
• 104-85-8 para-methylbenzonitrile 

Downstream Products

• 65772-26-1 3-morpholin-4-ylmethyl-2-p-tolyl-3H-quinazolin-4-one 
• 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 
• 16112-44-0 2-(4-methylphenyl)-4-phenyl-quinazoline 
• 1446786-00-0 2-(4-methylphenyl)-4-(4-methylphenyl)quinazoline 
• 121513-89-1 4-(4-methoxyphenyl)-2-(p-tolyl)quinazoline 
• 1520087-38-0 4-(4-chlorophenyl)-2-(p-tolyl)quinazoline 

Relevant academic research and scientific papers

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.

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.

Aerobic primary and secondary amine oxidation cascade by a copper amine oxidase inspired catalyst

Herein, we report a bioinspired catalytic system for the one-pot cascade oxidation of a native primary amine and anin situgenerated non-native secondary amine. The catalyst consists of ano-quinone cofactor phd (1,10-phenanthroline-5,6-dione) and a copper ion and operates under ambient air conditions. Quinazolin-4(3H)-ones, which are common pharmacophores present in numerous pharmaceuticals and bioactive compounds, were synthesized in high yields. A detailed kinetic and mechanistic study elucidates the role of the catalyst in the multi-step oxidative cascade reaction.

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).

Design, synthesis, characterization, enzymatic inhibition evaluations, and docking study of novel quinazolinone derivatives

In this study, novel quinazolinone derivatives 7a-n were synthesized and evaluated against metabolic enzymes including α-glycosidase, acetylcholinesterase, butyrylcholinesterase, human carbonic anhydrase I, and II. These compounds exhibited high inhibitory activities in comparison to used standard inhibitors with Ki values in the range of 19.28–135.88 nM for α-glycosidase (Ki value for standard inhibitor = 187.71 nM), 0.68–23.01 nM for acetylcholinesterase (Ki value for standard inhibitor = 53.31 nM), 1.01–29.56 nM for butyrylcholinesterase (Ki value for standard inhibitor = 58.16 nM), 10.25–126.05 nM for human carbonic anhydrase I (Ki value for standard inhibitor = 248.18 nM), and 13.46–178.35 nM for human carbonic anhydrase II (Ki value for standard inhibitor = 323.72). Furthermore, the most potent compounds against each enzyme were selected in order to evaluate interaction modes of these compounds in the active site of the target enzyme. Cytotoxicity assay of the title compounds 7a-n against cancer cell lines MCF-7 and LNCaP demonstrated that these compounds do not show significant cytotoxic effects.

Ruthenium(II)-catalyzed C?C/C?N coupling of 2-arylquinazolinones with vinylene carbonate: Access to fused quinazolinones

In this work, ruthenium(II)-catalyzed C?C/C?N annulation of 2-arylquinazolinones with vinylene carbonate is reported to synthesize fused quinazolinones. This catalytic system tolerates a wide range of substrates with excellent functional-group compatibility. In this transformation, the vinylene carbonate acts as an ethynol surrogate without any external oxidant involved. Furthermore, preliminary mechanistic studies were conducted, and a plausible catalytic cycle was also proposed.