449745-74-8

Usage

Compound class

Quinazolinone

Contains

Nitro group, benzylsulfanyl group, quinazolinone ring structure

Usage

Building block in the synthesis of pharmaceutical compounds and agrochemicals

Biological activities

Potential anticancer, antifungal, and antibacterial properties

Research status

More research needed to fully understand its biological effects and potential applications.

Upstream product

• 13906-09-7 2-thioxo-2,3-dihydro-1H-quinazolin-4-one 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 21563-73-5 2-aminobenzoyl chloride 
• 118-92-3 anthranilic acid 
• 13906-09-7 2-mercapto-3H-quinazolin-4-one 

Downstream Products

• 1429046-00-3 C₂₉H₂₀N₄O₂S₂ 
• 874637-89-5 2-(4-nitro-benzylsulfanyl)-3H-quinazolin-4-thione 
• 1429045-78-2 C₂₉H₂₁N₇O₂S₂ 

Relevant academic research and scientific papers

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.

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.