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Eleven novel oxiranyl and thiiranyl phenolic compounds were synthesized as potential antitumor agents using epichlorohydrin and epithiohydrin in the presence of K2CO3. Cytotoxicities were found in range of IC50 values of 2.5-14.8 μM, which was partially attributed to topoisomerase II inhibition. Bis-thiiranyl anthraquinone analog, 19 showed more cytotoxicity against MDA-MB-231 (breast cancer cell) and PC3 (prostate cancer cell) after 24 and/or 48 h and more potent topoisomerase II inhibitory activity than etoposide.

Design, Synthesis, Antitumor Activity and Mode of Action of Novel Oxiranyl and Thiiranyl Phenol Derivatives