Synthesis and antitumor activities of novel dibenzo[b,d]furan–imidazole hybrid compounds

• Novel dibenzo[b,d]furan–imidazole hybrid compounds were prepared.
• Hybrid compound 60 was found to be the most potent derivative.
• Hybrid compound 49 was found to be more selective against A549 and SMMC-7721.
• The structure–activity relationship results of hybrid compounds were summarized.
• Hybrid 60 can induce the G1 phase cell cycle arrest and apoptosis in SMMC-7721 cells.

A series of novel hybrid compounds between dibenzo[b,d]furan and imidazole has been prepared and evaluated in vitro against a panel of human tumor cell lines. The results suggest that the existence of benzimidazole ring, and the substitution of the imidazolyl-3-position with a naphthylacyl or 4-methoxyphenacyl group, were vital for modulating cytotoxic activity. In particular, hybrid compound 60 was found to be the most potent derivatives against all of human tumor cell lines investigated, while compound 49 was found to be more selective against breast carcinoma (MCF-7) and myeloid liver carcinoma (SMMC-7721). Compound 60 can induce the G1 phase cell cycle arrest and apoptosis in SMMC-7721 cells.

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