Brief introduction of 1,1′-Diacetylferrocene

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A new family of heterometallic compounds 3-6 containing ferrocenyl and platinum(ii) centers has been synthesized by reaction of 1-beta- aminoethylferrocene (1) and 1,1?-bis(beta-aminoethyl)ferrocene (2) with Pt(ii) precursors. Using K2[PtCl4] as the Pt(ii) source, the cis-square-planar neutral compounds [Fe{eta5-C 5H4(CH2)2NH2} 2PtCl2] (3) and [{Fe(eta5-C5H 4(CH2)2NH2)(eta5-C 5H5)}2PtCl2] (5) were obtained. Reaction of cis-[PtCl2(dmso)2] with 1 and 2 resulted in the displacement of dmso and chloride ligands from the platinum coordination sphere, affording the cationic and neutral compounds [Fe{eta5- C5H4(CH2)2NH2} 2Pt(dmso)Cl]Cl (4) and [Fe(eta5-C5H 4(CH2)2NH2)(eta5-C 5H5)Pt(dmso)Cl2] (6). Compounds 3-6 were thoroughly characterized using multinuclear (1H, 13C, 195Pt) NMR, IR spectroscopy, ESI mass spectrometry and elemental analysis. Single-crystal X-ray analysis of heterometallic 6 confirmed the cis geometry of the molecule and revealed that the platinum atom is held in a perfect square-planar geometry. The electrochemical behaviour of the heterometallic compounds 3-6, which has been examined by cyclic (CV) and square wave (SWV) voltammetries in dichloromethane and dmso solution, is characterized by the reversible one-electron oxidation of the ferrocene moieties. The results of the biological activity studies revealed that the organometallic complex 5 is active against all cell lines with GI50 values in the range 1.7-2.3 muM. When compared to the standard anticancer drug cisplatin, heterotrimetallic 5, possessing two aminoethylferrocenyl units coordinated to the Pt(ii) center, showed a greater activity profile in the colon cancer cell line. Cell cycle studies revealed that the new mixed compound exhibits a mechanism of action different to cisplatin.

Heterometallic platinum(ii) compounds with beta-aminoethylferrocenes: Synthesis, electrochemical behaviour and anticancer activity

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Reference£º
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion