69976-31-4

Basic information

• Product Name: 3-(2,4-dichlorophenyl)-2H-chromen-2-one
• Synonyms: 3-(2,4-dichlorophenyl)-2H-chromen-2-one
• CAS NO: 69976-31-4
• Molecular Weight: 291.133
• Mol File: 69976-31-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 3-(2,4-dichlorophenyl)-2H-chromen-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2,4-dichlorophenyl)-2H-chromen-2-one(69976-31-4)
• EPA Substance Registry System: 3-(2,4-dichlorophenyl)-2H-chromen-2-one(69976-31-4)

Safety Data

• Hazardous Substances Data: 69976-31-4(Hazardous Substances Data)

Upstream product

• 10465-91-5 3-(4-chlorophenyl)-2H-chromen-2-one 
• 19719-28-9 2,4-dichlorophenylacetic acid 
• 90-02-8 salicylaldehyde 

Relevant articles and documents

Palladium-Catalyzed Weakly Coordinating Lactone-Directed C-H Bond Functionalization of 3-Arylcoumarins: Synthesis of Bioactive Coumestan Derivatives

A palladium-catalyzed highly regioselective ortho-selective C-H functionalization of 3-arylcoumarins has been developed. The method utilizes the weakly coordinating lactone as a directing group. The versatility of the strategy is highlighted by developing methodologies for alkenylation, halogenation, fluoroalkoxylation, and hydroxylation. Different functional groups were well tolerated, and functionalized coumarins were obtained in moderate to high yields. The method also showed good selectivity for monofunctionalization versus difunctionalization. The generated ortho-hydroxy derivatives were cyclized in the presence of DDQ, thus developing a simple and fast method for the synthesis of bioactive coumestan from 3-arylcoumarins.

3-phenylcoumarins as inhibitors of HIV-1 replication

We have synthesized fourteen 3-phenylcoumarin derivatives and evaluated their anti-HIV activity. Antiviral activity was assessed on MT-2 cells infected with viral clones carrying the luciferase gene as reporter. Inhibition of HIV transcription and Tat function were tested on cells stably transfected with the HIV-LTR and Tat protein. Six compounds displayed NF-κB inhibition, four resulted Tat antagonists and three of them showed both activities. Three compounds inhibited HIV replication with IC50 values 25 μM. The antiviral effect of the 4-hydroxycoumarin derivative 19 correlates with its specific inhibition of Tat functions, while compound 8, 3-(2-chlorophenyl) coumarin, seems to act through a mechanism unrelated to the molecular targets considered in this research.