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A novel series of bis(furan‐based chalcone) derivatives linked to aliphatic linkers, with the furan units at the A‐ or B‐rings, were synthesized and evaluated as anticancer agents. Chalcones 5 a–c in which the furan ring designed to be a B‐ring were obtained from the Knoevenagel condensation reactions of the appropriate bis(acetyl) compounds 3 a–c with two equivalents of furan‐2‐aldehyde. Likewise, the condensation of bis(aldehydes) 7 a–c with two equivalents of 2‐acetylfuran afforded the corresponding chalcones 9 a–c, in which the furan rings represent the A‐rings of the chalcones, in excellent yields. The synthesized compounds have been fully characterized by ¹H‐NMR, ¹³C‐NMR, and elemental analysis. The in vitro anticancer activity of the prepared compounds was tested against A549, HCT116, HePG2, PC3, A431 and BJ1 cell lines using MTT assay, gene expression analysis of skin and lung …