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- Title
Synthesis and cytotoxic evaluation of some new [1,3]dioxolo[4,5-g]chromen-8-one derivatives.
- Authors
Alipour, Eskandar; Mousavi, Zinatsadat; Safaei, Zahra; Pordeli, Mahboobeh; Safavi, Maliheh; Firoozpour, Loghman; Mohammadhosseini, Negar; Saeedi, Mina; Kabudanian Ardestani, Sussan; Shafiee, Abbas; Foroumadi, Alireza
- Abstract
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. 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-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. Results: 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. 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.
- Subjects
BREAST tumors; CELL lines; ANALYTICAL chemistry; COLORIMETRY; FLAVONOIDS; MICROSCOPY; RESEARCH funding; PLANT extracts; ISOFLAVONES; CYTOTOXINS
- Publication
DARU: Journal of Pharmaceutical Sciences, 2014, Vol 22, p22
- ISSN
1560-8115
- Publication type
Article
- DOI
10.1186/2008-2231-22-41