RESUMEN

Benzoylthiourea derivatives feature several donor atoms capable of coordinating to metal centers. We report here a series of Ru(η6 -p-cymene) complexes employing benzoylthiourea derivatives as ligands. Such ligands often coordinate to metal centers through their S and O donor atoms. We isolated complexes where the ligands were mono- or bidentately coordinated to Ru involving the S donor atom and surprisingly in bidentate coordination mode a deprotonated thiourea nitrogen resulting in a 4-membered ring structure around the metal center. DFT calculations were used to explain the differences in coordination behavior. These were complemented by stability studies and biological investigations of the compounds as anticancer agents. Several of the synthesized derivatives exhibited significant cell growth inhibitory activity, with the complexes featuring bidentate ligands being more potent than their monodentate counterparts. This can be explained by the higher stability of the former under the conditions employed in cell culture assays.

Asunto(s)

Antineoplásicos/química , Antineoplásicos/farmacología , Complejos de Coordinación/química , Complejos de Coordinación/farmacología , Rutenio/farmacología , Tiourea/farmacología , Antineoplásicos/síntesis química , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Complejos de Coordinación/síntesis química , Teoría Funcional de la Densidad , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Ligandos , Estructura Molecular , Rutenio/química , Relación Estructura-Actividad , Tiourea/análogos & derivados , Tiourea/química

RESUMEN

In the mol-ecule of the title compound, C(16)H(14)O(2), the aromatic rings are oriented at a dihedral angle of 78.49 (3)°. The heterocyclic ring adopts a twist conformation. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into chains along the c axis.

RESUMEN

In the mol-ecule of the title compound, C(16)H(11)FOS, the benzene ring is oriented at a dihedral angle of 89.68 (3)° with respect to the planar [maximum deviation 0.009 (2) Å] isocoumarin ring system. An intra-molecular C-H⋯S inter-action results in the formation of a planar five-membered ring. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into chains parallel to the c axis. A π-π contact between the isocoumarin rings [centroid-centroid distance = 3.818 (3) Å] may further stabilize the structure.