Rhenium mixed-ligand complexes with S,N,S-tridentate thiosemicarbazone/thiosemicarbazide ligands
| Autor: | Adelheid Hagenbach, Victor M. Deflon, Pedro I. S. Maia, Hung Huy Nguyen, Silke Bergemann, Ronald Gust, Ulrich Abram |
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| Rok vydání: | 2013 |
| Předmět: |
Thiosemicarbazones
Denticity Stereochemistry Cell Survival Molecular Conformation chemistry.chemical_element Crystallography X-Ray Ligands Medicinal chemistry Inorganic Chemistry chemistry.chemical_compound Deprotonation Coordination Complexes Humans Chelation Sodium Azide Semicarbazone Ligand MOLÉCULA (SÍNTESE) Rhenium Semicarbazides chemistry MCF-7 Cells Sodium azide Ammonium thiocyanate |
| Zdroj: | Repositório Institucional da USP (Biblioteca Digital da Produção Intelectual) Universidade de São Paulo (USP) instacron:USP |
| ISSN: | 1477-9234 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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