Novel (−)-goniofufurone mimics: Synthesis, antiproliferative activity and SAR analysis

Bojana Srećo Zelenović, Sladjana Kekezović, Mirjana Popsavin, Vesna Kojić, Goran Benedeković, Velimir Popsavin


Divergent syntheses of novel (–)-goniofufurone mimics with an alko­xymethyl group as the side chain have been accomplished from d-glucose in nine synthetic steps and in overall yields 6.7–8.7 %. Their in vitro antipro­life­rative activity was evaluated against eight human tumour cell lines as well as a single normal cell line. All analogues demonstrated powerful to good anti­pro­liferative effects toward all malignant cell lines under evaluation. Against the HL-60 cell line, all mimics showed increased activities being 27- to 1604-fold more potent than the lead compound, (–)-goniofufurone. Remarkably, the maj­or­ity of synthesized analogues displayed higher or similar activity to the com­mercial antitumour agent doxorubicin (DOX) against A549 cell line. The most potent compound exhibited 196-fold stronger cytotoxicity than DOX in the culture of this cell line.


D-glucose; antitumour agents; goniofufurone mimics; cytotoxic lactones, structure–activity relationships


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