586345-75-7

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 6-[[4-oxo-5-(phenylmethoxy)-4H-pyran-2-yl]methoxy]-2-phenyl-
• CAS NO: 586345-75-7
• Molecular Formula: C28H20O6
• Molecular Weight: 452.463
• Mol File: 586345-75-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 6-[[4-oxo-5-(phenylmethoxy)-4H-pyran-2-yl]methoxy]-2-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 6-[[4-oxo-5-(phenylmethoxy)-4H-pyran-2-yl]methoxy]-2-phenyl-(586345-75-7)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 6-[[4-oxo-5-(phenylmethoxy)-4H-pyran-2-yl]methoxy]-2-phenyl-(586345-75-7)

Safety Data

• Hazardous Substances Data: 586345-75-7(Hazardous Substances Data)

Upstream product

• 100-44-7 benzyl chloride 
• 89539-54-8 5-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-one 
• 6665-83-4 6-hydroxyflavone 
• 15771-06-9 5-benzyloxy-2-hydroxymethyl-4H-pyran-4-one 
• 501-30-4 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one 

Relevant articles and documents

Synthesis and cytotoxicity evaluation of metal-chelator-bearing flavone, carbazole, dibenzofuran, xanthone, and anthraquinone

2-(Aryloxymethyl)-5-benzyloxy-1-methyl-1H-pyridin-4-ones 8a-8g, 2-(aryloxymethyl)-5-hydroxy-4H-pyran-4-ones 9a-9g, and 2-(aryloxymethyl)-5-hydroxy-1-methyl-1H-pyridin-4-ones 10a-10g were prepared from the known 5-benzyloxy-2-(hydroxymethyl)pyran-4-one (3) in a good overall yield. These compounds were evaluated in vitro against a three-cell lines panel consisting of MCF7 (breast), NCI-H460 (lung), and SF-268 (CNS), and the active compounds passed on for evaluation in the full panel of 60 human tumor cell lines derived from nine cancer cell types. The results indicated that 5-hydroxy derivatives are more favorable than their corresponding 5-benzyloxy precursors (10a-10g vs. 8a-8g), and 1-methyl-1H-pyridin-4-ones are more favorable than their corresponding pyran-4(1H)-ones (10a-10g vs. 9a-9g). Among these three types of compounds, 2-(aryloxymethyl)-5-hydroxy-1-methyl-1H-pyridin-4-ones 10a-10g were the most cytotoxic; they inhibited the growth of almost all the cancer cells tested. On the contrary, compound 8a (a mean GI50 = 27.8 μM), 8b (38.5), 8d (11.0), and 8e (30.5) are especially active against the growth of SK-MEL-5 (a melanoma cancer cell) with a GI50 of 0.01, 5.65, 0.55, and 0.03 μM, respectively (cf. Table 2).