55168-26-8

Upstream product

• 1776-08-5 (E)-3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one 
• 541-41-3 chloroformic acid ethyl ester 
• 4198-01-0 3-(α-Hydroxybenzoyl)chromone 
• 14386-66-4 2-(formylacetyl)phenol 
• 39079-62-4 chromone-3-carboxylic acid 
• 17422-74-1 3-Formylchromone 
• 1469-94-9 1-(2-hydroxyphenyl)-3-phenyl-1,3-propanedione 
• 692283-33-3 1-(3,4-dimethoxy-phenyl)-3-(2-hydroxy-4-methoxy-phenyl)-propane-1,3-dione 
• 4233-35-6 3-(3,4-Dimethoxyphenyl)-1-(2-hydroxyphenyl)-propane-1,3-dione 
• 5067-22-1 1-(2-hydroxyphenyl)-3-(4-methylphenyl)propane-1,3-dione 
• 104387-22-6 1-(2-hydroxyphenyl)-5-phenyl-4-pentene-1,3-dione 
• 4010-33-7 2-acetylphenyl benzoate 
• 67858-33-7 2-acetylphenyl-3,4-dimethoxybenzoate 
• 74766-95-3 Zimtsaeure-<2-acetyl-phenyl >-ester 

Relevant academic research and scientific papers

Synthesis and Antimicrobial Activity of (Z)-3-{[3-Oxobenzofuran-2(3H)-ylidene]methyl}-4H-chromen-4-one Derivatives

A series of (Z)-3-{[3-oxobenzofuran-2(3H)-ylidene]methyl}-4H-chromen-4-one derivatives have been synthesized from 2-hydroxyl acetophenones by the Vilesmeier–Haack reaction, Claisen–Schmidt reaction and mercury(II) acetate/cupric bromide. All the synthesized compounds were characterized by IR, 1H and 13C NMR, and mass spectral data and elemental analysis. The products were tested for their in vitro antimicrobial activity.

One-Pot Synthesis of Benzopyran-4-ones with Cancer Preventive and Therapeutic Potential

A one-pot synthesis of novel benzopyran-4-ones is described. In a tandem reaction, organobase-catalysed Michael addition of R1COCH2COR2 on chromone-3-carboxylic acid led to decarboxylation and pyran-4-one ring opening of the latter. This was followed by chromone-and/or chromanone ring closure of the resulting Michael adducts when R1 is an ortho-hydroxyaryl group. Antioxidant testing of 14 derivatives identified strong antiradical properties of chromanones 3o-r (2.1-3.1 μmol Trolox equiv./μmol compound in the DPPH assay). Chromanones 3p and 3r and 2-styrylchromone 3k were also most potent in inducing the cytoprotective Keap1-Nrf2 signalling pathway in a reporter gene assay (fivefold induction at concentrations 3 μM). Of the seven compounds evaluated for antiproliferative activities, 3k and 3r were the most active, inhibiting leukaemia K562 cell proliferation by 50 % after 72 h at concentrations of 4.5 and 7.9 μM, whereas normal peripheral blood mononuclear cells were not affected. Chromanones 3p and 3r and 2-styrylchromones 3k potently activate the Nrf2 response in the AREc32 cell line at low micromolar concentrations (C5 3 μM). Compounds 3k and 3r are also the most active in inhibiting cell proliferation by 50 % after 72 h incubation at concentrations of 4.5 and 7.7 μM, whereas normal peripheral blood mononuclear cells were not affected.

Behaviour of o-hydroxyacetophenones towards action of POCl3/DMF (Vilsmeier reagent) in presence of BF3.Et2O: A novel observation in the synthesis of chromones

The influence of the presence of BF3.Et2O on the Vilsmeier reactions of o-hydroxyacetophenones and related naphthophenones has been examined. A significant and novel feature of this study is the development of new and facile procedure for the synthesis of some chromones. The reaction offers a first example of monoformylation of o-hydroxyacetophenones.

Benzopyrans : Part 40 - Alumina mediated transformations of 4-oxo-4H-1- benzopyran-3-carbaldehyde, -3-carboxylic acid and their 2-methylhomologues

In contact with alumina, the title aldehyde 1 (R = H, Me, Cl) gives the chromones 5 and 9,12 whereas the acid 2 affords the chromones 7, 10 and acetophenone 23. Alumina converts the aldehyde 3 to the xanthone 14, and the corresponding acid 4 to the chromone 8 and diketone 24.

On the Chemistry of α-Formyl-2-hydroxyacetophenone

The title compound 1 undergoes cyclization and self-condensation in the presence of dil.NaOH yielding chromone (2) and/or 1-(3-chromonyl)-2-(2-hydroxybenzoyl)ethene (3).With benzaldehyde in the presence of piperidine in boiling ethanol, 1 reacts both by cyclization, and self-condensation combined with cyclization to give 2, 3 and bis(3-chromonylphenyl)methane (5).If less than 0.1 M aq.NaOH is used 1 and benzaldehyde produces 3-(α-hydroxybenzoyl)chromone (4) which can also be converted into 5. - keywords: Acetophenone, α-formyl-2-hydroxy; Condensation reaction, base-promoted; Chromones

Thermal Dimerization of 2-Hydroxychromanones to 1-(2-Hydroxybenzoyl)-2-(4-oxo-4H-1-benzopyran-3-yl)ethylene Derivatives: An Unusual Observation

o-Hydroxyacetophenone derivatives on condensation with ethyl formate in the presence of sodium give the corresponding 2-hydroxychromanones (I), which when heated above their melting points afford 1-(2-hydroxybenzoyl)-2-(4-oxo-4H-1-benzopyran-3-yl)ethylene