6344-77-0

Basic information

• Product Name: 2-benzylsulfanyl-1H-quinazolin-4-one
• Synonyms: 2-benzylsulfanyl-1H-quinazolin-4-one
• CAS NO: 6344-77-0
• Molecular Formula: C₁₅H₁₂N₂OS
• Molecular Weight: 268.3336
• Mol File: 6344-77-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 212-213 °C(Solv: ethanol (64-17-5))
• Boiling Point: 452.9 °C at 760 mmHg
• Flash Point: 227.7 °C
• Appearance: /
• Density: 1.27 g/cm³
• Vapor Pressure: 2.17E-08mmHg at 25°C
• Refractive Index: 1.674
• PKA: -0.30±0.20(Predicted)
• CAS DataBase Reference: 2-benzylsulfanyl-1H-quinazolin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-benzylsulfanyl-1H-quinazolin-4-one(6344-77-0)
• EPA Substance Registry System: 2-benzylsulfanyl-1H-quinazolin-4-one(6344-77-0)

Safety Data

• Hazardous Substances Data: 6344-77-0(Hazardous Substances Data)

Usage

General Description

2-benzylsulfanyl-1H-quinazolin-4-one is a chemical compound that belongs to the class of quinazolinone derivatives. It has potential pharmacological and biological activities, making it a valuable target for drug development. The compound has been studied for its anti-inflammatory, analgesic, and anticonvulsant properties. It has also shown potential in the treatment of various diseases such as cancer, cardiovascular diseases, and neurological disorders. The compound's structure consists of a quinazolinone core with a benzylsulfanyl group attached at the 2-position, which contributes to its biological activities and potential therapeutic uses. Further research and development of 2-benzylsulfanyl-1H-quinazolin-4-one could lead to the discovery of novel drugs with important medical applications.

InChI:InChI=1/C15H12N2OS/c18-14-12-8-4-5-9-13(12)16-15(17-14)19-10-11-6-2-1-3-7-11/h1-9H,10H2,(H,16,17,18)

Upstream product

• 13906-09-7 2-mercapto-3H-quinazolin-4-one 
• 134-20-3 2-carbomethoxyaniline 
• 16024-82-1 methyl 2-isothiocyanatobenzoate 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 21563-73-5 2-aminobenzoyl chloride 
• 118-92-3 anthranilic acid 
• 13906-09-7 2-thioxo-2,3-dihydro-1H-quinazolin-4-one 

Downstream Products

• 90852-43-0 C₁₇H₁₆N₂OS 
• 1152-07-4 2-(4-methoxyphenyl)-3H-quinazolin-4-one 
• 1022-45-3 2-phenyl-4(3H)-quinazolinone 
• 1452776-66-7 2-(benzylsulfanyl)quinazolin-4-yl 4-cyanobenzenesulfonate 
• 1452776-65-6 2-(benzylsulfanyl)quinazolin-4-yl 4-methylbenzenesulfonate 
• 1429045-76-0 C₂₉H₂₂N₆S₂ 
• 96727-53-6 2-benzylsulfanyl-3H-quinazolin-4-thione 
• 1429045-98-6 C₂₉H₂₁N₃S₂ 

Relevant articles and documents

2-((3,5-Dinitrobenzyl)thio)quinazolinones: Potent Antimycobacterial Agents Activated by Deazaflavin (F420)-Dependent Nitroreductase (Ddn)

Swapping the substituents in positions 2 and 4 of the previously synthesized but yet undisclosed 5-cyano-4-(methylthio)-2-arylpyrimidin-6-ones 4, ring closure, and further optimization led to the identification of the potent antitubercular 2-thio-substituted quinazolinone 26. Structure-activity relationship (SAR) studies indicated a crucial role for both meta-nitro substituents for antitubercular activity, while the introduction of polar substituents on the quinazolinone core allowed reduction of bovine serum albumin (BSA) binding (63c, 63d). While most of the tested quinazolinones exhibited no cytotoxicity against MRC-5, the most potent compound 26 was found to be mutagenic via the Ames test. This analogue exhibited moderate inhibitory potency against Mycobacterium tuberculosis thymidylate kinase, the target of the 3-cyanopyridones that lies at the basis of the current analogues, indicating that the whole-cell antimycobacterial activity of the present S-substituted thioquinazolinones is likely due to modulation of alternative or additional targets. Diminished antimycobacterial activity was observed against mutants affected in cofactor F420 biosynthesis (fbiC), cofactor reduction (fgd), or deazaflavin-dependent nitroreductase activity (rv3547), indicating that reductive activation of the 3,5-dinitrobenzyl analogues is key to antimycobacterial activity.

Conversion of 2-thioxo-2,3-dihydroquinazolin-4(1H)-ones to N(3)-unsubstituted 2-(het)arylquinazolin-4(3H)-ones by copper-mediated Pd-catalysed cross-coupling reactions

With the purpose of searching for new heterocyclic building blocks, a new method to access N(3)-unsubstituted 2-(het)arylquinazolin-4(3H)-ones from 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives was developed. The synthetic protocol was based on the copper-mediated palladium-catalysed cross-coupling reactions of 2-thioxo-2,3-dihydroquinazolin-4(1H)-ones with (het)arylstannanes or their S-benzylated derivatives with (het)arylboronic acids, using CuBr·Me2S and CuMeSal as promoters, respectively. A similar transformation was applied for the preparation of 2-aryl[1]benzothieno[3,2-d]pyrimidin-4(3H)-ones.

Synthesis and evaluation of quinazoline derivatives as phosphodiesterase 7 inhibitors

The latest scientific findings concerning PDE7 and PDE4 inhibition suggest that selective small-molecule inhibitors of both enzymes could provide a novel approach to treat a variety of immunological diseases. In this context, we describe a new series of quinazoline derivatives from quinazolin-4-thiones which include a substituted biphenyl fragment. Some of these compounds show inhibitory potencies at sub-micromolar levels against the catalytic domain of PDE7.