Design, synthesis and anticancer activity of novel hybrid compounds between benzofuran and N-aryl piperazine

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Abstract

A series of novel hybrid compounds between benzofuran and N-aryl piperazine have been designed and prepared. These derivatives were evaluated for their in vitro anti-tumor activity against a panel of human tumor cell lines by MTT assay. The results demonstrated that amide derivatives were more bioactive than sulfonamide compounds in general, and that chloro or trifluoromethyl substituent was vital for modulating cytotoxic activity. In particular, compound 13 was found to be the most potent compound against 4 strains human tumor cell lines, and exhibited cytotoxic activity selectively against Hela (0.03 μM).

Graphical abstract

A series of novel hybrid compounds between benzofuran and N-aryl piperazine have been designed and prepared. These derivatives were evaluated for their in vitro anti-tumor activity against a panel of human tumor cell lines by MTT assay. The results demonstrated that amide derivatives were more bioactive than sulfonamide compounds in general, and that chloro or trifluoromethyl substituent was vital for modulating cytotoxic activity. In particular, compound 13 was found to be the most potent compound against 4 strains human tumor cell lines, and exhibited cytotoxic activity selectively against Hela (0.03 μM).

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Acknowledgments

This work was financially supported by the Natural Science Foundation of China (81460624) and the Application Basic Research Program of Yunnan Province (2014FZ087).

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    Fig. 1 represents examples of potent biologically active pyrazolopyridines V(VI), pyrazolopyrimidines VII(VIII) and pyridopyrazolopyrimidines IX(X).[31,32,35-38] Moreover, piperazine-benzofuran hybrids exhibit fascinating medicinal efficacies as antimicrobial,[39-41] anticancer,[42-44] anti-inflammatory,[44] antidepressant,[45] anticancer,[44,46] antiplatelet,[47] and anticholinesterase activities,[47] as well as mycobacterium tuberculosis DNA GyrB inhibitory activity.[48] In the context of our efforts to develop simple synthetic routes for bis(N-heterocycles),[49-58] we report herein the regioselective synthesis of novel piperazine-linked bis(pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidine) hybrids, bearing benzofuran moieties.

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