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Novel Imino Thioether Complexes of Platinum(II): Synthesis, Structural Investigation, and Biological Activity

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posted on 19.02.2016, 08:30 by Paolo Sgarbossa, Silvia Mazzega Sbovata, Roberta Bertani, Mirto Mozzon, Franco Benetollo, Cristina Marzano, Valentina Gandin, Rino A. Michelin
The reactions of the nitrile complexes cis- and trans-[PtCl2(NCR)2] (R = Me, Et, CH2Ph, Ph) with an excess of ethanethiol, EtSH, in the presence of a catalytic amount of n-BuLi in tetrahydrofuran (THF), afforded in good yield the bis-imino thioether derivatives cis-[PtCl2{E-N­(H)C­(SEt)­R}2] (R = Me (1), Et (2), CH2Ph (3), Ph (4)) and trans-[PtCl2{E-N­(H)C­(SEt)­R}2] (R = Me (5), Et (6), CH2Ph (7), Ph (8)). The imino thioether ligands assumed the E configuration corresponding to a cis addition of the thiol to the nitrile triple bond. The spectroscopic properties of these complexes have been reported along with the molecular structures of 1, 2, and 7 as established by X-ray crystallography which indicated that these compounds exhibit square-planar coordination geometry around the platinum center. Four N–H···Cl intermolecular contacts (N–H···Cl ca. 2.5–2.7 Å) between each chlorine atom and the N–H proton of the imino thioether ligand gave rise to “dimers” Pt2Cl4L4 (L = imino thioether) formed by two PtCl2L2 units. The cytotoxic properties of these new platinum­(II) complexes were evaluated against various human cancer cell lines. Among all derivatives, trans-[PtCl2{E-N­(H)C­(SEt)­CH2Ph}2] showed the greatest in vitro cytotoxic activity being able to decrease cancer cell viability roughly 3-fold more effectively than cisplatin.