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A series of 4α/4β-imidazolyl podophyllotoxin analogues have been designed and synthesized. All of the compounds were evaluated for their anticancer activity against a panel of three human cancer cell lines. Within the cell lines tested, some of the synthesized compounds showed promising anticancer activity. Compound 12, in particular, exhibited remarkable cytotoxicity, demonstrating effects against all tumor cell lines, including the K562/ADM cell line.

In title compound, C16H17FN2O2, the cyclo­hexane ring adopts a chair conformation.. The crystal packing is stabilized by weak π–π stacking inter­actions [centroid–centroid distance = 3.503 (5) Å] and inter­molecular C—H⋯O, N—H⋯O and N—H⋯F hydrogen-bond inter­actions.

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In the title compound, C16H20N2O3, the crystal packing is stabilized by weak π–π stacking inter­actions [centroid–centroid distances = 3.577 (9) and 3.693 (9) Å] and inter­molecular C—H⋯O and N—H⋯O hydrogen-bond inter­actions. The C atoms of the N-isopropyl group are disordered over two sets of sites with occupancies of 0.61(3) and 0.39(3).