19816-54-7

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 7-methoxy-3-(4-nitrophenyl)-
• CAS NO: 19816-54-7
• Molecular Formula: C16H11NO5
• Molecular Weight: 297.267
• Mol File: 19816-54-7.mol

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 7-methoxy-3-(4-nitrophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 7-methoxy-3-(4-nitrophenyl)-(19816-54-7)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 7-methoxy-3-(4-nitrophenyl)-(19816-54-7)

Safety Data

• Hazardous Substances Data: 19816-54-7(Hazardous Substances Data)

Upstream product

• 57272-98-7 2-hydroxy-4-methoxy-4'-nitro-deoxybenzoin 
• 103-70-8 Formanilid 
• 636-98-6 p-nitrobenzene iodide 
• 73220-33-4 3-(dimethylamino)-1-(4-ethoxy-2-hydroxyphenyl)prop-2-en-1-one 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 24067-17-2 4-nitrophenylboronic acid 
• 73220-42-5 3-iodo-7-methoxy-chromen-4-one 
• 108-46-3 recorcinol 
• 555-21-5 4-Nitrophenylacetonitrile 
• 15485-63-9 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone 
• 15485-80-0 7-hydroxy-3-(4-nitrophenyl)-4H-chromen-4-one 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 486-63-5 isoformononetin 
• 97472-93-0 3-(4-aminophenyl)-7-methoxy-4H-chromen-4-one 

Relevant articles and documents

Synthesis of novel isoflavone/benzo-δ-sultam hybrids as potential anti-inflammatory drugs

A small series of novel isoflavone/benzo-δ-sultam hybrids was synthesised and evaluated as potential anti-inflammatory and neuroprotective drugs in LPS-activated BV2 microglia. The benzo-δ-sultam core was constructed in a two-step reaction by coupling 2-halobenzenesulfonamide derivatives with terminal alkynes, followed by a 6-endo-dig cyclisation. The synthesised compounds, including precursors and hybrids, were tested for their ability to inhibit NO and TNF-α production in LPS-stimulated BV2 microglial cells, and the results are promising. The most potent hybrid reduces the NO production to 41%, and the TNF-α to 34% at 20 μM final concentration in the well.

Structural studies on bioactive compounds. 40.1 synthesis and biological properties of fluoro-, methoxyl-, and amino-substituted 3-phenyl-4H-1-benzopyran-4-ones and a comparison of their antitumor activities with the activities of related 2-phenylbenzothiazoles

A new series of fluoro-, methoxyl-, and amino-substituted isoflavones have been synthesized as potential antitumor agents based on structural similarities to known flavones and isoflavones (quercetin and genistein respectively) and antitumor 2-phenylbenzothiazoles. Target compounds were synthesized using palladium-catalyzed coupling methodologies to construct the central aryl carbon-carbon single bond. The new isoflavone derivatives were tested for in vitro activity in human breast (MDA-MB-468 and MCF-7) and colon (HT29 and HCT-116) cancer cell lines. Low micromolar GI50 values were obtained in a number of cases, with the MDA-MB-468 cell line being the most sensitive overall. Notably, significant potentiation of growth inhibitory activity (GI50 1 μM for 12d, 12f, 12h, 12k, 121, 12o but not the methylene-bridged derivative 12i) was observed when MDA-MB-468 cells were co-incubated with TBDD, a powerful inducer of cytochrome P450 (CYP)-1A1 activity, suggesting that isoflavone derivatives can act as substrates for CYP1A1 bioactivation.