13906-05-3

Basic information

• Product Name: 3-BENZYL-2-THIOXO-2,3-DIHYDRO-4(1H)-QUINAZOLINONE
• Synonyms: 3-BENZYL-2-THIOXO-2,3-DIHYDRO-4(1H)-QUINAZOLINONE;3-Benzyl-2-thioxo-2,3-dihydro-1H-quinazolin-4-one;3-(benzyl)-2-thioxo-1H-quinazolin-4-one;3-(phenylmethyl)-2-sulfanylidene-1H-quinazolin-4-one;3-(phenylmethyl)-2-thioxo-1H-quinazolin-4-one;3-benzyl-2-sulfanylidene-1H-quinazolin-4-one
• CAS NO: 13906-05-3
• Molecular Formula: C₁₅H₁₂N₂OS
• Molecular Weight: 268.33358
• Product Categories: quinazolinone
• Mol File: 13906-05-3.mol
• Article Data: 28

Chemical Properties

• Melting Point: >250
• Boiling Point: 441.6 °C at 760 mmHg
• Flash Point: 220.9 °C
• Appearance: /
• Density: 1.36 g/cm³
• Vapor Pressure: 5.37E-08mmHg at 25°C
• Refractive Index: 1.724
• PKA: 11.13±0.20(Predicted)
• CAS DataBase Reference: 3-BENZYL-2-THIOXO-2,3-DIHYDRO-4(1H)-QUINAZOLINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BENZYL-2-THIOXO-2,3-DIHYDRO-4(1H)-QUINAZOLINONE(13906-05-3)
• EPA Substance Registry System: 3-BENZYL-2-THIOXO-2,3-DIHYDRO-4(1H)-QUINAZOLINONE(13906-05-3)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 13906-05-3(Hazardous Substances Data)

Usage

General Description

3-Benzyl-2-thioxo-2,3-dihydro-4(1H)-quinazolinone is a chemical compound that falls under the category of quinazolines, which are heterocyclic compounds consisting of two fused six-member rings, a benzene ring, and a pyrimidine ring. This specific compound has a benzyl group attached to the third carbon atom and a thioxo group on the second carbon atom. As a thioxo derivative, it contains sulfur, which replaces the oxygen atom in the corresponding oxo derivative. Quinazolinone derivatives, including 3-benzyl-2-thioxo-2,3-dihydro-4(1H)-quinazolinone, have been studied for their potential pharmacological activities, such as anticancer, anti-inflammatory, anticonvulsant, and antimicrobial properties, although further research is needed to understand their precise mode of action and potential side effects.

InChI:InChI=1/C15H12N2OS/c18-14-12-8-4-5-9-13(12)16-15(19)17(14)10-11-6-2-1-3-7-11/h1-9H,10H2,(H,16,19)

Upstream product

• 622-78-6 Benzyl isothiocyanate 
• 118-92-3 anthranilic acid 
• 28144-70-9 anthranilic acid amide 
• 134-20-3 2-carbomethoxyaniline 
• 4314-19-6 bis(1H-benzo[d][1,2,3]triazol-1-yl)methanethione 
• 100-46-9 benzylamine 
• 610-15-1 2-nitrobenzamide 
• 118-48-9 isatoic anhydride 
• 333-20-0 potassium thioacyanate 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 56624-44-3 3-benzylthiocarbamoylsulfanyl-propionic acid methyl ester 
• 5115-14-0 monobenzyldithiocarbamate sodium 
• 75-15-0 carbon disulfide 
• 5471-20-5 2-amino-N-benzylbenzamide 

Downstream Products

• 5388-11-4 3-benzyl-3H-quinazolin-4-one 
• 1688-81-9 3-benzyl-2-(methylsulphanyl)-3H-quinazolin-4-one 
• 74395-78-1 3-benzyl-2-hydrazino-3H-quinazolin-4-one 
• 77437-24-2 C₂₃H₂₁N₅OS 
• 77437-22-0 C₂₂H₁₉N₅OS 

Relevant articles and documents

Application of Deep Eutectic Solvents in the Synthesis of Substituted 2-Mercaptoquinazolin-4(3H)-Ones: A Comparison of Setected Green Chemistry Methods

In this study, deep eutectic solvents (DESs) were used as green and eco-friendly media for the synthesis of substituted 2-mercaptoquinazolin-4(3H)-ones from different anthranilic acids and aliphatic or aromatic isothiocyanates. A model reaction on anthranilic acid and phenyl isothiocyanate was porformed in 20 choline chloride-based DESs at 80 °C to find the best solvent. Based on the product yield, choline chloride-urea (1:2) DES was found to be the most effective, while DESs acted both as solvents and catalysts. Desired compounds were prepared with moderate to good yields using stirring, microwave-assisted, and ultrasound-assisted synthesis. Significantly, higher yields were obtained with mixing and ultrasonication (16-76%), while microwave-induced synthesis showed lower effectiveness (13-49%). The specific contribution of this research is the use of DESs in combination with the above-mentioned green techniques for the synthesis of a wide range of derivatives. The structures of the synthesized compounds were confirmed by1H and13C NMR spectroscopy.

Quinazolinone-dihydropyrano[3,2-b]pyran hybrids as new α-glucosidase inhibitors: Design, synthesis, enzymatic inhibition, docking study and prediction of pharmacokinetic

A series of new quinazolinone-dihydropyrano[3,2-b]pyran derivatives 10A-L were synthesized by simple chemical reactions and were investigated for inhibitory activities against α-glucosidase and α-amylase. New synthesized compounds showed high α-glucosidase inhibition effects in comparison to the standard drug acarbose and were inactive against α-amylase. Among them, the most potent compound was compound 10L (IC50 value = 40.1 ± 0.6 μM) with inhibitory activity around 18.75-fold more than acarboase (IC50 value = 750.0 ± 12.5 μM). This compound was a competitive inhibitor into α-glucosidase. Our obtained experimental results were confirmed by docking studies. Furthermore, the cytotoxicity of the most potent compounds 10L, 10G, and 10N against normal fibroblast cells and in silico druglikeness, ADME, and toxicity prediction of these compounds were also evaluated.

The natural-based optimization of kojic acid conjugated to different thio-quinazolinones as potential anti-melanogenesis agents with tyrosinase inhibitory activity

Melanin pigment and melanogenesis are a two-edged sword. Melanin has a radioprotection role while melanogenesis has undesirable effects. Targeting the melanogenesis pathway, a series of kojyl thioether conjugated to different quinazolinone derivatives were designed, synthesized, and evaluated for their inhibitory activity against mushroom tyrosinase. All the synthesized compounds were screened for their anti-tyrosinase activity and all derivatives displayed better potency than kojic acid as the positive control. In this regard, 5j and 5h as the most active compounds showed an IC50 value of 0.46 and 0.50 μM, respectively. In kinetic evaluation against tyrosinase, 5j depicted an uncompetitive inhibition pattern. Designed compounds also exhibited mild antioxidant capacity. Moreover, 5j and 5h achieved good potency against the B16F10 cell line to reduce the melanin content, whilst showing limited toxicity against malignant cells. The proposed binding mode of new inhibitors evaluated through molecular docking was consistent with the results of structure–activity relationship analysis.