447451-05-0

Upstream product

• 870-63-3 prenyl bromide 
• 447451-03-8 7-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-2-phenyl-chromen-4-one 
• 106009-51-2 5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl benzoate 
• 480-40-0 5,7-dihydroxy-2-phenyl-chromen-4-one 

Relevant academic research and scientific papers

Effects of flavonoids on cell proliferation and caspase activation in a human colonic cell line HT29: An SAR study

A library of 42 natural and synthetic flavonoids has been screened for their effect on cell proliferation and apoptosis in a human colonic cell line (HT-29). Examples of different classes of flavonoids have been screened, and the effects of hydroxylation, methoxylation and/or C-alkylation at various positions in the A- and B-rings have been assessed. Flavones and flavonols possess greater antiproliferative activity than chalcones and flavanones. With respect to structural modification of flavonoids, C-isoprenylation was by far the most effective, with substitution at the 8-position and longer chains, such as geranyl giving the best results. Finally, most compounds that significantly reduced cell survival also increased caspase activity, suggesting that at least part of their antiproliferative activity might be attributable to an apoptotic response.

Regioselective syntheses of 6-(1,1-dimethylallyl)- and 8-(3,3-dimethylallyl) chrysins

The first regioselective syntheses of 6-(1,1-dimethylallyl)- and 8-(3,3-dimethylallyl) chrysins have been designed. Claisen rearrangement of protected 5-O-(3,3-dimethylallyl) chrysin in N,N-diethylaniline at 200-217°C gave selective access to the 8-(3,3-dimethylallyl) isomer. Similar rearrangement in N,N-diethylbutylamine at 140-160°C, or in cycloheptane/Eu(fod)3 at 100°C, led to the formation of the 6-(1,1-dimethylallyl) isomer. Four different protecting groups for position 7 of chrysin have been compared, and found to follow the order of interest Bz>MOM>TBDPS>MEM.