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Background  Homoisoflavonoids are naturally occurring compounds belong to flavonoid classes possessing various biological properties such as cytotoxicity. In this work, an efficient strategy for the synthesis of novel homoisoflavonoids, [1,3]dioxolo[4,5- g ]chromen-8-ones, was developed and all compounds were evaluated for their cytotoxic activities on three breast cancer cell lines.    Methods  Our synthetic route started from benzo[ d ][1,3]dioxol-5-ol which was reacted with 3-bromopropanoic acid followed by the reaction of oxalyl chloride to afford 6,7-dihydro-8 H -[1,3]dioxolo[4,5- g ]chromen-8-one. The aldol condensation of the later compound with aromatic aldehydes led to the formation of the title compounds. Five novel derivatives  4a-e  were tested for their cytotoxic activity against three human breast cancer cell lines including MCF-7, T47D, and MDA-MB-231 using the MTT assay.    Results  Among the synthesized compounds, 7-benzylidene-6,7-dihydro-8 H -[1,3]dioxolo[4,5- g ]chromen-8-one ( 4a ) exhibited the highest activity against three cell lines. Also the analysis of acridine orange/ethidium bromide staining results revealed that 7-benzylidene-6,7-dihydro-8 H -[1,3]dioxolo[4,5- g ]chromen-8-one ( 4a ) and 7-(2-methoxybenzylidene)-6,7-dihydro-8 H -[1,3]dioxolo[4,5- g ]chromen-8-one ( 4b ) induced apoptosis in T47D cell line.    Conclusion  Finally, the effect of methoxy group on the cytotoxicity of compounds  4b-4d  was investigated in and it was revealed that it did not improve the activity of [1,3]dioxolo[4,5- g ]chromen-8-ones against MCF-7, T47D, and MDA-MB-231.

Synthesis and cytotoxic evaluation of some new[1,3]dioxolo[4,5-g]chromen-8-one derivatives