Synthesis and In Vitro Cytotoxic Activity of Novel [1,3] Dioxolo[4,5-g]Chromen-8-ones as a Chalcone-Like Agent

Document Type: Research Paper



In this investigation, new structures based on homoisoflavonoids were designed. Homoisoflavonoids are considered as an important class of flavonoids with various biological properties such as cytotoxicity. A new series of benzylidene-6,7-dihydro-8H-[1,3]dioxolo[4,5-g] chromen-8-one derivatives were developed and their cytotoxic activities evaluated for all compounds on three human breast cancer cell lines. Benzo[d][1,3]dioxol-5-ol was chosen as a substrate and reacted with 3-bromopropanoic acid to form an intermediate which turns to 6,7-dihydro-8H-[1,3]dioxolo[4,5-g]chromen-8-one after Feridel-Crafts reaction with oxalyl chloride. In the end, title compounds were produced by aldol condensation of later compound under acidic condition with aromatic aldehydes in moderate yields. Eight novel derivatives were tested for their activities against all human breast cancer cell lines including MCF- 7, T47-D and MDA-MB-231 using MTT assay. After all tests on synthesized products, we can reach to this point that (E)-7-(3-bromo-4,5-dimethoxybenzylidene)-6,7-dihydro-8H-[1,3] dioxolo[4,5-g]chromen-8-one 4a presents the highest cytotoxicity in all three cell lines as a result of its shorter aliphatic tail in benzylidene moiety.