1579990-06-9

Basic information

• Product Name: 2-benzyl-5-hydroxy-4H-chromen-4-one
• Synonyms: 2-benzyl-5-hydroxy-4H-chromen-4-one
• CAS NO: 1579990-06-9
• Molecular Weight: 252.269
• Mol File: 1579990-06-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-benzyl-5-hydroxy-4H-chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-benzyl-5-hydroxy-4H-chromen-4-one(1579990-06-9)
• EPA Substance Registry System: 2-benzyl-5-hydroxy-4H-chromen-4-one(1579990-06-9)

Safety Data

• Hazardous Substances Data: 1579990-06-9(Hazardous Substances Data)

Upstream product

• 699-83-2 2,6-dihydroxylacetophenone 
• 103-82-2 phenylacetic acid 
• 78646-28-3 2′-hydroxy-6′-methoxymethoxyacetophenone 
• 101-97-3 Ethyl 2-phenylethanoate 

Relevant articles and documents

Synthesis and Characterization of 5-Hydroxy-2-(2-phenylethyl)chromone (5-HPEC) and Its Analogues as Non-nitrogenous 5-HT2B Ligands

The involvement of the neurotransmitter serotonin (5-HT) in numerous physiological functions is often attributed to the diversity of receptors with which it interacts. Ligands targeting serotonin receptor 2B (5-HT2B) have received renewed interest for their potential to help understand the role of 5-HT2B in migraines, drug abuse, neurodegenerative diseases, and irritable bowel syndrome. To date, most of the ligands targeting 5-HT2B have been nitrogen-containing compounds. The natural product 5-hydroxy-2-(2-phenylethyl)chromone (5-HPEC, 5) has been shown previously to act as a non-nitrogenous antagonist for the 5-HT2B receptor (pKi = 5.6). This report describes further progress on the study of the structure-activity relationship of both naturally occurring and synthetic compounds bearing the 2-(2-phenylethyl)chromone scaffold at the 5-HT2B receptor. The inhibitory activity of the newly synthesized compounds (at 10 μM) was tested against each of the 5-HT2 receptors. Following this assay, the binding affinity and antagonism of the most promising compounds were then evaluated at 5-HT2B. Among all the analogues, 5-hydroxy-2-(2-phenylpropyl)chromone (5-HPPC, 22h) emerged as a new lead compound, showing a 10-fold improvement in affinity (pKi = 6.6) over 5-HPEC with reasonable antagonist properties at 5-HT2B. Additionally, ligand docking studies have identified a putative binding pocket for 5-HPPC and have helped understand its improved affinity. (Figure Presented).

5-Hydroxy-2-(2-phenylethyl)chromone (5-HPEC): A novel non-nitrogenous ligand for 5-HT2B receptor

Chromones are a class of natural products found in almost every known terrestrial plant with over 4000 naturally occurring derivatives having been isolated and structurally elucidated. Recently, 5-hydroxy-2-(2-phenylethyl) chromone (5-HPEC), isolated from Imperata cylindrical, showed neuroprotective activity against glutamate induced excitotoxicity in primary cultures of rat cortical cells. In comparison to other naturally occurring neuroprotective chromones, 5-HPEC contains fewer hydroxyl groups. Here we report our most recent characterization on this interesting natural product against a number of CNS receptors for the purpose to identify the potential molecular targets that may be related to its biological activity. Based on our studies, including radiobinding assays, calcium flux functional assays and molecular modeling studies, 5-HPEC may represent a type of novel nonnitrogenous ligands to the 5-HT2B receptor.