4842-56-2

Upstream product

• 1157-39-7 7-methoxy-3-(4-methoxyphenyl)-4H-chromen-4-one 
• 121-97-1 4-Methoxypropiophenone 
• 100-09-4 4-methoxybenzoic acid 
• 2901-41-9 2-(4-methoxyphenyl)ethyl propionate 
• 942-54-1 2-(4-methoxyphenyl)propanoic acid 
• 4842-48-2 (αR)-angolensin 
• 21255-69-6 O-desmethylangolensin 
• 74-88-4 methyl iodide 
• 487-49-0 1-(2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone 
• 39604-64-3 1-(2-hydroxy-4-methoxyphenyl)-2-(4-methoxyphenyl)ethanone 
• 186581-53-3 diazomethane 
• 642-39-7 angolensin 

Downstream Products

• 4842-55-1 (+/-)-1-(2,4-Dimethoxy-phenyl)-2-(4-methoxy-phenyl)-propan 
• 5012-91-9 (+/-)-1-(2-Hydroxy-4-methoxy-phenyl)-2-(4-methoxy-phenyl)-propan 
• 5012-93-1 opt.-inakt.-1-(2-Hydroxy-4-methoxy-phenyl)-2-(4-methoxy-phenyl)-propan-1-ol 

Relevant academic research and scientific papers

A versatile synthesis of O-desmethylangolensin analogues from methoxy-substituted benzoic acids

The synthesis of O-desmethylangolensin (O-DMA) analogues from methoxy-substituted benzoic acids was described. Treatment of methoxy-substituted benzoic acids with 2 equiv of ethyllithium afforded methoxypropiophenones, which were subsequently transformed to ethyl 2-(methoxyphenyl)propionates via 1,2-rearrangement of the methoxyphenyl group using Pb(OAc)4/HClO4 in triethyl orthoformate. After hydrolysis with KOH, the 2-(methoxyphenyl)propionic acids were reacted with di- 2-pyridyl carbonate to afford 2-pyridyl 2-(methoxyphenyl)propionates, which were acylated with methoxy-substituted phenylmagnesium bromides to give methoxy-α-methyldesoxybenzoins. The methoxy groups of these compounds were selectively or fully demethylated using boron tribromide to give diverse O-DMA analogues in high yields.

Synthesis, structure-activity relationship analysis and kinetics study of reductive derivatives of flavonoids as Helicobacter pylori urease inhibitors

In a continuing study for discovering urease inhibitors based on flavonoids, nineteen reductive derivatives of flavonoids were synthesized and evaluated against Helicobacter pylori urease. Analysis of structure-activity relationship disclosed that 4-deoxy analogues are more potent than other reductive products. Out of them, 4′,7,8-trihydroxyl-2-isoflavene (13) was found to be the most active with IC50 of 0.85 μM, being over 20-fold more potent than the commercial available urease inhibitor, acetohydroxamic acid (AHA). Kinetics study revealed that 13 is a competitive inhibitor of H. pylori urease with a Ki value of 0.641 μM, which is well matched with the results of molecular docking. Biological evaluation and mechanism study of 13 suggest that it is a good candidate for discovering novel anti-gastritis and anti-gastric ulcer agent.

Regioselectivity of methylation of O-demethylangolensin [1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)propan-1-one]. An expedient synthesis of angolensin

1-(2,4-Dihydroxyphenyl)-2-(4-hydroxyphenyl)propan-1-one (1), also known as 2',4',4''-trihydroxy-α-methyldeoxybenzoin or O-demethylangolensin (ODMA), is regioselectively 4-O-alkylated at ring B via the triphenolate anion by one equivalent of methyl iodide

Synthesis of α-methyldeoxybenzoins

Reduction of hydroxy and/or methoxy-substituted isoflavones using LiAlH4 in refluxing THF provides an easy access to a number of α-methyldeoxybenzoins, possible metabolites of phytoestrogens in man. The synthesis of O-demethylangolensin 2b, 6′-hydroxyangolensin 2c, angolensin 2d, 1-(2,4-dihydroxyphenyl)-2-phenylpropan-1-one 2e, 1-(2-hydroxy-4-methoxyphenyl)-2-(4-hydroxyphenyl)propan-1-one2f, 4′-O-methylangolensin 2g, 1-(2-hydroxy-4-methoxyphenyl)-2-phenylpropan-1-one 2h, and 1-(2-hydroxyphenyl)-2-phenylpropan-1-one 2i is described. The Royal Society of Chemistry 1999.

A Facile Synthesis of α-Methyldesoxybenzoins Including Racemates of Natural Angolensin, 2-O-Methylangolensin and 4-O-Methylangolensin

Methylation of four different 2-hydroxydesoxybenzoins ( 1a, 1c, 1d, 1f) separately with methyl iodide in the presence of dry potassium carbonate and acetone at 35-40 deg C affords both C-methyl-(2a, 2d) and O-methyl-(1b, 1e) derivatives.However, 1a provid