N,N-[(diethylamino)(thiocarbonyl)]-substituted benzamidine ligands have been synthesized from the reaction of N,N-[(diethylamino)(thiocarbonyl)]benzimidoyl chloride with functionalized amines such as 2-aminophenol and 2-picolylamine. The reaction of N,N-[(diethylamino)(thiocarbonyl)]-2-hydroxyphenylbenzamidine (H 2 L 1 ) with ruthenium(II) precursor [RuHCl(CO)(PPh 3 ) 3 ] afforded complex 1 of the type [Ru(L 1 )(CO)(PPh 3 ) 2 ] in which the ligand coordinated in tridentate ONS mode. The reaction of H 2 L 1 with copper precursor [Cu(CH 3 COO)(PPh 3 ) 2 ] induced C═N bond cleavage of the ligand and afforded complex 3 of the type [Cu(1,1-DT) (Cl)(PPh 3 ) 2 ] (1,1-DT = 1,1-diethylthiourea) in which the ligand coordinated in a monodentate fashion. The ligand N,N-[(diethylamino)(thiocarbonyl)]-2picolylbenzamidine (HL 2 ) reacted with ruthenium(II) and copper(I) precursors to form complex 2 of the type [Ru(1,1-DT)(Cl 2 )(CO)(PPh 3 ) 2 ] and complex 3, respectively, in which the ligand underwent C═N cleavage and coordinated in a monodentate fashion via C═S group. In complexes 1 and 2, the two triphenylphosphine co-ligands coordinated in trans position whereas, in complex 3, the two triphenylphosphine co-ligands coordinated in cis position. All the compounds were characterized using infrared, UV-visible, ( 1 H, 13 C, 31 P) NMR, ESI-MS and elemental analyses. The molecular structures of ligand H 2 L 1 and complexes 1-3 were determined using X-ray crystallography, which confirmed the coordination mode of the ligands with metals. The crystal structure of complexes 1 and 2 revealed a distorted octahedral geometry around the ruthenium ion and the structure of complex 3 indicated a tetrahedral geometry around the copper ion. With the X-ray structures, density functional theory computations were carried out to determine the electronic structure of the compounds. The interactions of complexes 1-3 with calf thymus DNA and bovine serum albumin protein were investigated using UV-visible and fluorescence spectroscopic and viscometric methods. Catecholase-and phosphatase-like activities promoted by complexes 1-3 under physiological conditions have been studied. In vitro anticancer activities have been demonstrated by MTT assay, acridine orange/ethidium bromide and diamidino-2-phenylindole staining against various cancerous cell lines.
In the molecule of the title compound, C17H17NO5S, the two aromatic rings are oriented at an angle of 30.13 (10)°. The ethyl acetate group assumes an extended conformation. Molecules are linked into C(7) chains running along the a axis by intermolecular C—H⋯O hydrogen bonds, and the chains are crosslinked via C—H⋯π interactions, with the sulfonyl-bound phenyl ring acting as an acceptor.
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