479667-52-2

Basic information

• Product Name: (Z)-4-((4,6-dimethoxy-3-oxobenzofuran-2(3H)ylidene)methyl)benzonitrile
• Synonyms: (Z)-4-((4,6-dimethoxy-3-oxobenzofuran-2(3H)ylidene)methyl)benzonitrile
• CAS NO: 479667-52-2
• Molecular Weight: 307.306
• Mol File: 479667-52-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (Z)-4-((4,6-dimethoxy-3-oxobenzofuran-2(3H)ylidene)methyl)benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-4-((4,6-dimethoxy-3-oxobenzofuran-2(3H)ylidene)methyl)benzonitrile(479667-52-2)
• EPA Substance Registry System: (Z)-4-((4,6-dimethoxy-3-oxobenzofuran-2(3H)ylidene)methyl)benzonitrile(479667-52-2)

Safety Data

• Hazardous Substances Data: 479667-52-2(Hazardous Substances Data)

Upstream product

• 4225-35-8 4,6-dimethoxycoumaranone 
• 105-07-7 4-cyanobenzaldehyde 

Relevant articles and documents

Dimethoxyaurones: Potent inhibitors of ABCG2 (breast cancer resistance protein)

A series of 4,6-dimethoxyaurones were synthesized by reacting 4,6-dimethoxybenzofuran-3(2H)-one with various benzaldehydes in a base-catalyzed aldol reaction. A Z configuration was assigned to the aurones based on spectroscopic and crystallographic data.

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.