27439-06-1

Basic information

• Product Name: 5-Hydroxy-3-[(4-hydroxyphenyl)methylene]benzofuran-2(3H)-one
• Synonyms: 5-Hydroxy-3-[(4-hydroxyphenyl)methylene]benzofuran-2(3H)-one;Marginalin
• CAS NO: 27439-06-1
• Molecular Formula: C₁₅H₁₀O₄
• Molecular Weight: 254.24
• Mol File: 27439-06-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-Hydroxy-3-[(4-hydroxyphenyl)methylene]benzofuran-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hydroxy-3-[(4-hydroxyphenyl)methylene]benzofuran-2(3H)-one(27439-06-1)
• EPA Substance Registry System: 5-Hydroxy-3-[(4-hydroxyphenyl)methylene]benzofuran-2(3H)-one(27439-06-1)

Safety Data

• Hazardous Substances Data: 27439-06-1(Hazardous Substances Data)

Upstream product

• 2688-48-4 5-Hydroxy-2-coumaranone 
• 123-08-0 4-hydroxy-benzaldehyde 
• 705-15-7 1-(2-hydroxy-5-methoxyphenyl)ethan-1-one 
• 2503-24-4 5-methoxybenzofuran-2(3H)-one 
• 74189-56-3 4-(tetrahydropyran-2-yloxy)benzaldehyde 

Downstream Products

• 131928-09-1 5-Hydroxy-3-[1-(4-hydroxy-phenyl)-meth-(E)-ylidene]-3H-benzofuran-2-one; compound with N,N'-bis-(3-amino-propyl)-butane-1,4-diamine 
• 131928-10-4 5-Hydroxy-3-[1-(4-hydroxy-phenyl)-meth-(E)-ylidene]-3H-benzofuran-2-one; compound with N¹-(3-amino-propyl)-butane-1,4-diamine 

Relevant articles and documents

Functionalized aurones as inducers of NAD(P)H:quinone oxidoreductase 1 that activate AhR/XRE and Nrf2/ARE signaling pathways: Synthesis, evaluation and SAR

The chemopreventive potential of functionalized aurones and related compounds as inducers of NAD(P)H:quinone oxidoreductase 1 (NQO1, EC 1.6.99.2) are described. Several 4,6-dimethoxy and 5-hydroxyaurones induced NQO1 activity of Hepa1c1c7 cells by 2-fold at submicromolar concentrations, making these the most potent inducers to be identified from this class. Mechanistically, induction of NQO1 was mediated by the activation of AhR/XRE and Nrf2/ARE pathways, indicating that aurones may be mixed activators of NQO1 induction or agents capable of exploiting the proposed cross-talk between the AhR and Nrf2 gene batteries. QSAR analysis by partial least squares projection to latent structures (PLS) identified size parameters, in particular those associated with non-polar surface areas, as an important determinant of induction activity. These were largely determined by the substitution on rings A and B. A stereoelectronic role for the exocyclic double bond as reflected in the E LUMO term was also identified. The electrophilicity of the double bond or its effect on the conformation of the target compound are possible key features for induction activity.

Inhibitory activities against topoisomerase I and II by isoaurostatin derivatives and their structure-activity relationships

Isoaurostatin A (IAS-A) isolated from Thermomonospora alba showed weak inhibition against topoisomerase (topo) I (IC50 = 307 μM). To get more strong inhibition, derivatives of IAS-A were prepared and their structure-activity relationships against topo I and II were investigated. The addition of hydroxyl group on aromatic rings increased the activities, 3-(3,4,5-trihydroxybenzylidene)-5-hydroxy-3H-benzofuran-2-one (IAS-9) showed strong inhibition (IC50 = 3 μM) against topo I. And also, the increasing of hydroxyl group increased growth inhibition against a variety of cancer cells, and IAS-9 showed most potent inhibition. Unlike camptothecin and etoposide, IAS-9 neither stabilized DNA-topo cleavable complex nor intercalated into DNA, and it inhibited topo I and II noncompetitively. The inhibitory activities also increased by opening of lactone ring in the molecule of IAS-9.