Abstract
A series of diiron/tetrairon compounds containing a S- or a Se-function (2a–d, 4a–d, 5a–b, 6), and the monoiron [FeCp(CO){SeC1(NMe2)C2HC3(Me)}] (3) were prepared from the diiron μ-vinyliminium precursors [Fe2Cp2(CO)( μ-CO){μ-η1: η3-C3(R’)C2HC1N(Me)(R)}]CF3SO3 (R = R’ = Me, 1a; R = 2,6-C6H3Me2 = Xyl, R’ = Ph, 1b; R = Xyl, R’ = CH2OH, 1c), via treatment with S8 or gray selenium. The new compounds were characterized by elemental analysis, IR and multinuclear NMR spectroscopy, and structural aspects were further elucidated by DFT calculations. The unprecedented metallacyclic structure of 3 was ascertained by single crystal X-ray diffraction. The air-stable compounds (3, 4a–d, 5a–b, 6) display fair to good stability in aqueous media, and thus were assessed for their cytotoxic activity towards A2780, A2780cisR, and HEK-293 cell lines. Cyclic voltammetry, ROS production and NADH oxidation studies were carried out on selected compounds to give insights into their mode of action.
Highlights
The serendipitous discovery of the anticancer properties of cisplatin led to a paradigm shift in the clinical treatment of cancer
Bridging vinyliminium ligand, 1 [39], obtained via the sequential assembly of an isocyanide and Recently, we reported on the antiproliferative behavior of diiron complexes comprising a an alkyne on Fe2 Cp2 (CO)4 (Scheme 1, Cp = η5 -C5 H5 ) [40,41,42]
Type 1 compounds possess some drug-like on a multigram scale from cost effective precursors, they are stable in water media, and their characteristics, i.e., they are based on a substantially nontoxic metal, they may be prepared on a solubility/lipophilicity can be regulated by an appropriate choice of ligand substituents
Summary
The serendipitous discovery of the anticancer properties of cisplatin led to a paradigm shift in the clinical treatment of cancer. Processes in we living organisms, disulphide and diselenide functions, whencomplexes incorporated within a a Recently, reported on the antiproliferative behavior of diiron comprising drug structure, have been demonstrated to induce antiproliferative and apoptotic effects [36,37,38]. Type 1 compounds possess some bridging vinyliminium ligand, 1 [39], obtained via the sequential assembly of an isocyanide and an drug-like characteristics, i.e., they are based on a substantially nontoxic metal, they may be prepared alkyne on Fe2Cp2(CO) (Scheme 1, Cp = η5-C5H5) [40,41,42]. Type 1 compounds possess some drug-like on a multigram scale from cost effective precursors, they are stable in water media, and their characteristics, i.e., they are based on a substantially nontoxic metal, they may be prepared on a solubility/lipophilicity can be regulated by an appropriate choice of ligand substituents.
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