14756-24-2

Basic information

• Product Name: 3',4'-DiMethoxy-α-naphthoflavone
• Synonyms: 3',4'-DiMethoxy-α-naphthoflavone;2-(3,4-Dimethoxyphenyl)-benzo[h]chromen-4-one;DiMNF;NSC 123391
• CAS NO: 14756-24-2
• Molecular Formula: C₂₁H₁₆O₄
• Molecular Weight: 332.34934
• Product Categories: Aromatics;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics, Heterocycles, Inhibitors, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 14756-24-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 513.8°C at 760 mmHg
• Flash Point: 227.3°C
• Appearance: white to tan/
• Density: 1.271g/cm³
• Vapor Pressure: 1.15E-10mmHg at 25°C
• Refractive Index: 1.65
• Storage Temp.: 2-8°C
• Solubility: DMSO: ≥13mg/mL
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
• CAS DataBase Reference: 3',4'-DiMethoxy-α-naphthoflavone(CAS DataBase Reference)
• NIST Chemistry Reference: 3',4'-DiMethoxy-α-naphthoflavone(14756-24-2)
• EPA Substance Registry System: 3',4'-DiMethoxy-α-naphthoflavone(14756-24-2)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 14756-24-2(Hazardous Substances Data)

Usage

Description

3',4'-DiMethoxy-α-naphthoflavone (DiMNF) is a selective aryl hydrocarbon receptor (AHR) modulator (SAhRM) with the chemical formula C18H14O3. It exhibits anti-inflammatory activity and has therapeutic potential in regulating the immune response to tumor formation. DiMNF suppresses cytokine-mediated complement factor gene expression through selective activation of the Ah receptor and represses estrogen-inducible transcription.

Uses

Used in Pharmaceutical Industry:
3',4'-DiMethoxy-α-naphthoflavone is used as a therapeutic agent for its potential in regulating the immune response to tumor formation. The expression is: 3',4'-DiMethoxy-α-naphthoflavone is used as a selective AHR modulator for suppressing cytokine-mediated complement factor gene expression and repressing estrogen-inducible transcription.
Used in Research and Development:
3',4'-DiMethoxy-α-naphthoflavone is used as a research compound for studying the role of aryl hydrocarbon receptor (AHR) in various biological processes, including inflammation and immune response regulation. The expression is: 3',4'-DiMethoxy-α-naphthoflavone is used as a research tool for investigating the mechanisms of AHR modulation and its effects on cytokine-mediated gene expression.
Used in Drug Discovery:
3',4'-DiMethoxy-α-naphthoflavone is used as a lead compound in the development of new drugs targeting the aryl hydrocarbon receptor (AHR) for potential applications in treating inflammation and immune-related disorders. The expression is: 3',4'-DiMethoxy-α-naphthoflavone is used as a lead compound for drug discovery in the development of novel AHR modulators with potential therapeutic applications.

References

1) Murray?et al. (2011),?Suppression of cytokine-mediated complement factor gene expression through selective activation of the Ah receptor with 3’,4’-dimethoxy-α-naphthoflavone;? Mol. Pharmacol.,?79?508 2) Narayanan?et al. (2012),?Selective aryl hydrocarbon receptor modulator-mediated repression of CD55 expression induced by cytokine exposure;? J. Pharmacol. Exp. Ther.,?342?345 3) Labrecque?et al. (2012),?Distinct roles for aryl hydrocarbon receptor nuclear translocator and ah receptor in estrogen-mediated signaling in human cancer cell lines;? PLoS One,?7(1)?e29545

InChI:InChI=1/C21H16O4/c1-23-18-10-8-14(11-20(18)24-2)19-12-17(22)16-9-7-13-5-3-4-6-15(13)21(16)25-19/h3-12H,1-2H3

Upstream product

• 711-79-5 1-hydroxy-2-acetonaphthone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 125574-13-2 (E)-3-(3,4-dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one 
• 74-88-4 methyl iodide 

Relevant articles and documents

Synthesis and biological evaluation of flavones and benzoflavones as inhibitors of BCRP/ABCG2

Multidrug resistance (MDR) often leads to a failure of cancer chemotherapy. Breast Cancer Resistance Protein (BCRP/ABCG2), a member of the superfamily of ATP binding cassette proteins has been found to confer MDR in cancer cells by transporting molecules with amphiphilic character out of the cells using energy from ATP hydrolysis. Inhibiting BCRP can be a solution to overcome MDR.We synthesized a series of flavones, 7,8-benzofl avones and 5,6-benzo flavones with varying substituents at positions 3, 3′ and 4′ of the (benzo)fl avone structure. All synthesized compounds were tested for BCRP inhibition in Hoechst 33342 and pheophorbide A accumulation assays using MDCK cells expressing BCRP. All the compounds were further screened for their P-glycoprotein (P-gp) and Multidrug resistance-associated protein 1 (MRP1) inhibitory activity by calcein AM accumulation assay to check the selectivity towards BCRP. In addition most active compounds were investigated for their cytotoxicity. It was observed that in most cases 7,8-benzoflavones are more potent in comparison to the 5,6-benzoflavones. In general it was found that presence of a 3-OCH3 substituent leads to increase in activity in comparison to presence of OH or no substitution at position 3. Also, it was found that presence of 3′,4′-OCH3 on phenyl ring lead to increase in activity as compared to other substituents. Compound 24, a 7,8-benzoflavone derivative was found to be most potent being 50 times selective for BCRP and showing very low cytotoxicity at higher concentrations.