54855-81-1

Basic information

• Product Name: 2-(METHYLSULFANYL)-4(3H)-QUINAZOLINONE
• Synonyms: 2-(METHYLSULFANYL)-4(3H)-QUINAZOLINONE;2-METHYLSULFANYL-3H-QUINAZOLIN-4-ONE;2-(METHYLTHIO)QUINAZOLIN-4(1H)-ONE;2-(Methylthio)quinazolin-4(3H)-one;2-Methylthio-4(3H)-quinazolinone;2-methylsulfanyl-1H-quinazolin-4-one;2-(methylsulfanyl)-3,4-dihydroquinazolin-4-one
• CAS NO: 54855-81-1
• Molecular Formula: C₉H₈N₂OS
• Molecular Weight: 192.24
• Mol File: 54855-81-1.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 355.5°C at 760 mmHg
• Flash Point: 168.8°C
• Appearance: /
• Density: 1.36g/cm³
• Vapor Pressure: 3.11E-05mmHg at 25°C
• Refractive Index: 1.685
• CAS DataBase Reference: 2-(METHYLSULFANYL)-4(3H)-QUINAZOLINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(METHYLSULFANYL)-4(3H)-QUINAZOLINONE(54855-81-1)
• EPA Substance Registry System: 2-(METHYLSULFANYL)-4(3H)-QUINAZOLINONE(54855-81-1)

Safety Data

• Hazardous Substances Data: 54855-81-1(Hazardous Substances Data)

Usage

Chemical Class

Quinazolinone derivatives

Physical Appearance

Yellow powder

Molecular Weight

212.25 g/mol

Common Uses

Building block in the synthesis of pharmaceuticals and bioactive compounds

Therapeutic Activities

Anti-inflammatory, antimicrobial, and anticancer properties

Potential Applications

Treatment of cancer, inflammation, and microbial infections

Value in Drug Discovery

Valuable chemical for drug discovery and development due to its potential therapeutic activities.

InChI:InChI=1/C9H8N2OS/c1-13-9-10-7-5-3-2-4-6(7)8(12)11-9/h2-5H,1H3,(H,10,11,12)

Upstream product

• 48141-61-3 2,4-bis(methylthio)quinazoline 
• 74-83-9 methyl bromide 
• 13906-09-7 2-thioxo-2,3-dihydro-1H-quinazolin-4-one 
• 74-87-3 methylene chloride 
• 80-48-8 methyl p-toluene sulfonate 
• 118-92-3 anthranilic acid 
• 74-88-4 methyl iodide 
• 13906-09-7 2-thio-4-ketotetrahydroquinazoline 
• 13906-09-7 2-mercapto-3,4-dihydro-4-quinazolone 
• 77-78-1 dimethyl sulfate 
• 13906-09-7 2-mercapto-3H-quinazolin-4-one 
• 13277-24-2 N-benzoyl-N'-(2-carboxyphenyl)thiourea 
• 28144-70-9 anthranilic acid amide 
• 82018-09-5 2-mercapto-4(3H)-quinazolinone sodium salt 

Downstream Products

• 4248-15-1 2-anilinoquinazolin-4(3H)-one 
• 124309-88-2 2-<(4-chloro-2-methylphenyl)amino>-4-quinazolinone 
• 58803-74-0 4-chloro-2-(methylthio)quinazoline 
• 212143-48-1 2-Methanesulfinyl-3H-quinazolin-4-one 
• 1356922-71-8 2-methylthio-4-(4'-methylselenobenzyl)aminoquinazoline 
• 139047-57-7 3-bromomethyl-5-methylthio-2,3-dihydroimidazo[1,2-c ]quinazoline 

Relevant articles and documents

Synthesis and intramolecular cyclization of 2-methylsulfanyl-4-oxo-3(4H)- quinazolinylacetohydrazide

Treatment of ambident sodium salt of 2-methylsulfanyl-4(3H)-quinazolinone with methyl bromoacetate resulted in N3-alkyl ester formation. Reaction of the resulted ester with hydrazine hydrate gave 2-methylsulfanyl-4- oxo-3(4H)-quinazolinyl)aceto

Regioselective sulfonylation and N- to O-sulfonyl migration of quinazolin-4(3H)-ones and analogous thienopyrimidin-4(3H)-ones

The sulfonylation of quinazolin-4(3H)-ones and related tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-ones with mesyl, tosyl, and p-cyanobenzenesulfonyl chloride was studied. A hydrogen substituent at 2-position directed the sulfonyl group to the N-3 position, while alkylsulfanyl or amino substituents led to sulfonylation of the carbonyl oxygen. The latter effect was attributed to steric influence and the positive mesomeric effect of the 2-substituent. An access to N-sulfonylated 2-substituted regioisomers was established. An unexpected 1,3-sulfonyl migration was observed and further analyzed. This process occurred as an intramolecular N- to O-shift as verified by kinetic and crossover experiments.

Design, synthesis, and structure-activity relationships of highly potent 5-HT3 receptor ligands

The 5-HT3 receptor, a pentameric ligand-gated ion channel (pLGIC), is an important therapeutic target. During a recent fragment screen, 6-chloro-N-methyl-2-(4-methyl-1,4-diazepan-1-yl)quinazolin-4-amine (1) was identified as a 5-HT3R hit fragment. Here we describe the synthesis and structure-activity relationships (SAR) of a series of (iso)quinoline and quinazoline compounds that were synthesized and screened for 5-HT3R affinity using a [3H]granisetron displacement assay. These studies resulted in the discovery of several high affinity ligands of which compound 22 showed the highest affinity (pKi > 10) for the 5-HT3 receptor. The observed SAR is in agreement with established pharmacophore models for 5-HT3 ligands and is used for ligand-receptor binding mode prediction using homology modeling and in silico docking approaches.