The synthesis and the antitumor activity and fluorescent properties screening of novel bisphosphonate conjugates with cytotoxic 3,5-bis((hetero)arylidene)-4-piperidone residues were performed. The facile and rapid synthetic route was based on the aza-Michael addition of NH-3,5-bis((hetero)arylidene)-4-piperidones to tetraethyl ethylidenebisphosphonate. The synthesized compounds displayed high inhibitory properties towards Caov3, A549, PC3, and KB 3-1 human carcinoma cell lines. Among those, compounds bearing 4-cyano-phenyl and 3-pyridinyl substituents were revealed as the most active drug candidates with IC(50) values in the range of 0.5-2.5 µM. Methylenebisphosphonate with 4-Me(2) N-C(6) H(4) groups in the piperidone framework possessing fluorescence properties may be of interest for visualization of BPs skeletal distribution and cellular uptake in bones and other tissues.

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The mol­ecule of the title compound, C15H18N4, adopts a trans conformation with respect to the diazo N=N bond. The dihedral angle between the benzene and pyridine rings in the mol­ecule is 8.03 (5)°. In the crystal, a weak C—H⋯π inter­action arranges the mol­ecules into a corrugated ribbon, with an anti­parallel orientation of neighboring mol­ecules propagating in the [100] direction.