18818-39-8

Basic information

• Product Name: 4(1H)-Quinazolinone, 2-(2-methylphenyl)-
• Synonyms: 2-o-Tolyl-3H-chinazolin-4-on;2-o-Tolyl-chinazolon-4;2-o-tolyl-3H-quinazolin-4-one
• CAS NO: 18818-39-8
• Molecular Formula: C15H12N2O
• Molecular Weight: 236.273
• Mol File: 18818-39-8.mol
• Article Data: 60

Chemical Properties

• CAS DataBase Reference: 4(1H)-Quinazolinone, 2-(2-methylphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4(1H)-Quinazolinone, 2-(2-methylphenyl)-(18818-39-8)
• EPA Substance Registry System: 4(1H)-Quinazolinone, 2-(2-methylphenyl)-(18818-39-8)

Safety Data

• Hazardous Substances Data: 18818-39-8(Hazardous Substances Data)

Upstream product

• 89-95-2 2-methyl-benzyl alcohol 
• 28144-70-9 anthranilic acid amide 
• 95-47-6 o-xylene 
• 4001-73-4 2-Bromobenzamide 
• 1885-29-6 anthranilic acid nitrile 
• 610-15-1 2-nitrobenzamide 
• 7341-24-4 2-methylbenzyl mercaptan 
• 95-49-8 2-methylchlorobenzene 
• 59525-13-2 N-(2-carbamoylphenyl)-2-methylbenzamide 
• 644-36-0 o-methylphenylacetic acid 
• 611-15-4 1-methyl-2-vinyl-benzene 
• 552-45-4 1-chloromethyl-2-methylbenzene 
• 89-93-0 ortho-methylbenzylamine 
• 615-37-2 ortho-methylphenyl iodide 

Downstream Products

• 108618-52-6 2-o-tolylquinazoline-4(3H)-thione 
• 1537878-94-6 1-methyl-5,6-diphenyl-8H-isoquinolino[1,2-b]quinazolin-8-one 

Relevant articles and documents

Quinazolinone derivatives: Synthesis and comparison of inhibitory mechanisms on α-glucosidase

In this study, eight quinazolinone derivatives were designed and synthesized. Their inhibitory activities on α-glucosidase were assessed in vitro. Two compounds: 2-(4-chlorophenyl)-quinazolin-4(3H)-one (CQ) and 2-(4-bromophenyl)-quinazolin-4(3H)-one (BQ) were found to be potent inhibitors of α-glucosidase with IC50values of 12.5 ± 0.1 μM and 15.6 ± 0.2 μM, respectively. Spectroscopy methods were performed to analyze the inhibitory mechanisms of both compounds on α-glucosidase. The results revealed that they reversibly inhibited α-glucosidase in a non-competitive manner. CQ and BQ could statically quench the fluorescence spectra by formation of an inhibitor-α-glucosidase complex. The interaction between CQ and α-glucosidase depended on hydrogen bonds, electrostatic and hydrophobic force, while the driving force of the binding between BQ and the enzyme was hydrophobic. The docking results showed that BQ was less active than CQ against α-glucosidase because of its weaker interaction with the enzyme. In brief, the quinazolinone derivatives identified in this work were potentially promising candidates for developing as novel anti-diabetic agents.

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.

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.