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Issue 14, 2013
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Rhenium mixed-ligand complexes with S,N,S-tridentate thiosemicarbazone/thiosemicarbazide ligands

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Abstract

Rhenium(V) complexes containing tridentate thiosemicarbazones/thiosemicarbazides (H2L1) derived from N-[N′,N′-dialkylamino(thiocarbonyl)]benzimidoyl chlorides with 4,4-dialkylthiosemicarbazides have been synthesized by ligand-exchange reactions starting from [ReOCl(L1)]. The chlorido ligand of [ReOCl(L1)] (4) is readily replaced and reactions with ammonium thiocyanate or potassium cyanide give [ReO(NCS)(L1)] (6) and [ReO(CN)(L1)] (7), respectively. The reaction of (NBu4)[ReOCl4] with H2L1 and two equivalents of ammonium thiocyanate, however, gives in a one-pot reaction [ReO(NCS)2(HL1)] (8), in which the pro-ligand H2L1 is only singly deprotonated. An oxo-bridged, dimeric nitridorhenium(V) compound of the composition [{ReN(HL1)}2O] (11) is obtained from a reaction of (NBu4)[ReOCl4], H2L1 and sodium azide. The six-coordinate complexes [ReO(L1)(Ph2btu)] (12), where HPh2btu is N,N-diphenyl-N′-benzoylthiourea, can be obtained by treatment of [ReOCl(L1)] with HPh2btu in the presence of NEt3. Studies of the antiproliferative effects of the [ReOX(L1)] system (X = Cl, NCS or CN) on breast cancer cells show that the lability of a monodentate ligand seems to play a key role in the cytotoxic activity of the metal complexes, while the substitution of this ligand by the chelating ligand Ph2btu completely terminates the cytotoxicity.

Graphical abstract: Rhenium mixed-ligand complexes with S,N,S-tridentate thiosemicarbazone/thiosemicarbazide ligands

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Supplementary files

Article information


Submitted
08 Dec 2012
Accepted
29 Jan 2013
First published
29 Jan 2013

Dalton Trans., 2013,42, 5111-5121
Article type
Paper

Rhenium mixed-ligand complexes with S,N,S-tridentate thiosemicarbazone/thiosemicarbazide ligands

P. I. D. S. Maia, H. H. Nguyen, A. Hagenbach, S. Bergemann, R. Gust, V. M. Deflon and U. Abram, Dalton Trans., 2013, 42, 5111
DOI: 10.1039/C3DT32950J

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