350982-88-6

Basic information

• Product Name: (2Z)-2-(4-chlorobenzylidene)-4,6-dimethoxy-1-benzofuran-3(2H)-one
• Synonyms: (2Z)-2-(4-chlorobenzylidene)-4,6-dimethoxy-1-benzofuran-3(2H)-one
• CAS NO: 350982-88-6
• Molecular Weight: 316.741
• Mol File: 350982-88-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (2Z)-2-(4-chlorobenzylidene)-4,6-dimethoxy-1-benzofuran-3(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2Z)-2-(4-chlorobenzylidene)-4,6-dimethoxy-1-benzofuran-3(2H)-one(350982-88-6)
• EPA Substance Registry System: (2Z)-2-(4-chlorobenzylidene)-4,6-dimethoxy-1-benzofuran-3(2H)-one(350982-88-6)

Safety Data

• Hazardous Substances Data: 350982-88-6(Hazardous Substances Data)

Upstream product

• 4225-35-8 4,6-dimethoxycoumaranone 
• 104-88-1 4-chlorobenzaldehyde 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 76554-31-9 3-(4-chlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 
• 155673-98-6 (E)-3-(4-chlorophenyl)-1-(2'-hydroxy-4',6'-dimethoxyphenyl)prop-2-en-1-one 

Relevant articles and documents

4-Hydroxy-6-methoxyaurones with high-affinity binding to cytosolic domain of P-glycoprotein

A series of 4-hydroxy-6-methoxyaurones and 4,6-dimethoxyaurones has been synthesised and tested for their binding affinity toward the nucleotide-binding domain of P-glycoprotein, an ABC (ATP-Binding Cassette) transporter which mediates the resistance of cancer cells to chemotherapy. These compounds differ from each other by the nature of the substituent on the aurone B-ring. The binding affinity seems to be linked to the nature of the substituent, as well as to the presence or the absence of a hydroxy group at position 4. The most active compounds were 4′-bromo-4-hydroxy-6-methoxyaurone and 4-hydroxy-4′-iodo-6-methoxyaurone.

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.

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.