Description
4''-hydroxy Chalcone is a chalcone metabolite with diverse biological activities. It is formed when chalcone is metabolized by the cytochrome (CYP) P450 isoform CYP1A1 or CYP2C6.
1 4''-hydroxy Chalcone is estrogenic in MCF-7 cells and is cytotoxic at concentrations higher than 100 nM. It inhibits TNF-α-induced NF-κB signaling and the trypsin-, chymotrypsin-, and caspase-like proteolytic activities of the 26S proteasome in K562 cells in a dose-dependent manner.
2 4''-hydroxy Chalcone reduces growth of K562, U937, and Jurkat cancer cell lines in a dose-dependent manner without effecting viability of peripheral blood mononuclear cells (PBMCs). It also inhibits glutathione reductase (GSH-RD; IC
50 = 47.3 μM)
in vitro in a reversible and non-competitive manner.
3
Synthesis
To the reaction vials were added p-hydroxyacetophenone (1 mmol) and benzaldehyde (2 mmol in Table 2; 1 mmol in Table 3), as well as the Mo10V2/SiO2 catalyst (loading of 40 wt%, of which Mo10V2 accounted for 19-32.5 wt%, and ICP analysis showed that the Mo content was slightly lower than stoichiometrically expected at the time of preparation, specifically 0.06 g, or (0.010 mol/mol Mo10V2 relative to the substrate ketone). The mixture was stirred and reacted at 50 °C for an appropriate time. The reaction process was monitored by thin layer chromatography (TLC) using hexane/ethyl acetate (10:4, v/v) as eluent. After completion of the reaction, ether (2 × 10 mL) was added to the reaction mixture and the catalyst was isolated by filtration. The catalyst was washed and dried for reuse. The filtrate was concentrated under reduced pressure to remove the solvent and separated by column chromatography to obtain pure 1-(4-hydroxyphenyl)-3-phenylprop-2-en-1-one.
References
[1] Journal of the American Chemical Society, 2018, vol. 140, # 3, p. 1011 - 1018
[2] Monatshefte fur Chemie, 2013, vol. 144, # 3, p. 361 - 367
[3] Journal of the Chilean Chemical Society, 2013, vol. 58, # 3, p. 1926 - 1929
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 8, p. 682 - 687
[5] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 4, p. 578 - 587
