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

• Published in: Daru Vol. 22; no. 5; p. 1
• Main Authors: Alipour, Eskandar, Mousavi, Zinatsadat, Safaei, Zahra, Pordeli, Mahboobeh, Safavi, Maliheh, Firoozpour, Loghman, Mohammadhosseini, Negar, Saeedi, Mina, Ardestani, Sussan Kabudanian, Shafiee, Abbas, oumadi, Alireza
• Format: Journal Article
• Language: English
• Published: New York Springer Nature B.V 01.05.2014
• Subjects: Apoptosis; Breast cancer; Cell culture; Cytotoxicity; Derivatives; Studies; Germany
• ISSN: 1560-8115; 2008-2231

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. This study 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-8H-(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. Among the synthesized compounds, 7-benzylidene-6,7-dihydro-8H-(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-8H-(1,3)dioxolo(4,5-g)chromen-8-one (4a) and 7-(2-methoxybenzylidene)- 6,7-dihydro-8H-(1,3)dioxolo(4,5-g)chromen-8-one (4b) induced apoptosis in T47D cell line.