Synthesis and cytotoxic activity of novel benzopyrano[3,2-c]chromene-6,8-dione derivatives

Springer Science and Business Media LLC - Tập 20 - Trang 466-474 - 2010
Abbas Shafiee1,2, Radineh Motamedi3, Omidreza Firuzi4, Savis Meili4, Ahmad Reza Mehdipour4, Ramin Miri4
1Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
2Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran
3Department of Chemistry, Payame Noor University, Delijan, Iran
4Medicinal & Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran

Tóm tắt

4-Hydroxycoumarins constitute the structural nucleus of many natural products, drugs, and pesticides. Promising biological properties in new families of synthetic coumarins were recently reported. Therefore, efficient synthesis of new benzopyrano[3,2-c]chromene-6,8-dione was undertaken and the structures of 15 compounds were confirmed by their IR, Mass, 1H-NMR, and C, H, N analysis. Then, the cytotoxic activities of these compounds were assessed on four different human cancer cell lines (Raji, HeLa, LS180, and MCF-7). The results showed that these compounds had weak-to-moderate antitumoral activities and their IC50 ranged from 49 to more than 100 μM. Among the compounds 9,10-dihydro-7-(3-methoxyphenyl)-7H,11H-benzopyrano[3,2-c]chromene-6,8-dione [4k] demonstrated the highest activity. Furthermore, conformational analysis revealed that ortho substituents were clearly different from meta and para substituents.

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