546093-05-4

Basic information

• Product Name: 5-HYDROXY-2-(4-METHYL-PIPERAZINE-1-CARBONYL)-CHROMEN-4-ONE
• Synonyms: 5-HYDROXY-2-(4-METHYL-PIPERAZINE-1-CARBONYL)-CHROMEN-4-ONE
• CAS NO: 546093-05-4
• Molecular Formula: C15H16N2O4
• Molecular Weight: 288.3
• Mol File: 546093-05-4.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-HYDROXY-2-(4-METHYL-PIPERAZINE-1-CARBONYL)-CHROMEN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-HYDROXY-2-(4-METHYL-PIPERAZINE-1-CARBONYL)-CHROMEN-4-ONE(546093-05-4)
• EPA Substance Registry System: 5-HYDROXY-2-(4-METHYL-PIPERAZINE-1-CARBONYL)-CHROMEN-4-ONE(546093-05-4)

Safety Data

• Hazardous Substances Data: 546093-05-4(Hazardous Substances Data)

Upstream product

• 109-01-3 1-methyl-piperazine 
• 53878-47-0 5-hydroxy-4-oxo-4H-chromene-2-carboxylic acid 
• 703-23-1 2'-hydroxy-6'-methoxyacetophenone 
• 699-83-2 2,6-dihydroxylacetophenone 
• 5527-76-4 ethyl 5-methoxy-4-oxo-4H-chromene-2-carboxylate 
• 5527-74-2 5-methoxy-4-oxo-4H-chromene-2-carboxylic acid 

Relevant articles and documents

Modulation of P-glycoprotein-mediated multidrug resistance by flavonoid derivatives and analogues

Flavonoid derivatives were synthesized and tested for their ability to modulate P-glycoprotein (Pgp)-mediated multidrug resistance (MDR) in vitro. These compounds belong to various flavonoid subclasses, namely: chromones, azaisoflavones, and aurones. Among the investigated compounds, three showed potent reversing activity. 2-(4-Methylpiperazin-1-ylcarbonyl)-5-hydroxychromone (4a), 5,7-dimethoxy-3-phenyl-4-quinolone (5), and 4,6-dimethoxyaurone (6) potentiated daunorubicin cytotoxicity on resistant K562 cells. They were also able to increase the intracellular accumulation of rhodamine-123, a fluorescent molecule which acts as a probe of P-glycoprotein-mediated MDR. This suggests that these compounds act, at least in part, by inhibiting P-glycoprotein activity. The most active compound, 5-hydroxy-2-(4-methylpiperazin- 1-ylcarbonyl)chromone (4a) was found to be a powerful reversal agent, more potent than cyclosporin A, used as the reference molecule. No effect was observed on MRP transport nor on cell proliferation. Little apoptosis was induced on K562S cells with 4a compared to K562R, probably due to the extrusion of the compound by Pgp.