Halfsandwich complexes of ruthenium(II), rhodium(III) and iridium(III) with N-substituted 3-hydroxy-2-methyl-4-pyridone ligands

Lang, Roland; Polborn, Kurt; Severin, Theodor; Severin, Kay

doi:10.1016/s0020-1693(99)00280-7

Cited by 33 publications

(26 citation statements)

References 35 publications

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“…This work amplifies and extends brief earlier reports of the preparation of tris-maltolate [21] and tris-1,2-dimethyl-3-hydroxy-4-pyridinonate [22] complexes of ruthenium(III)-the latter having the unexpected formulation Ru(dmpp) 3 Cl. Our investigation also complements studies on the ruthenium(II) and ruthenium(III) pair of complexes [Ru(malt)Cl 2 (PPh 3 ) 2 ] x [23], and on several arene-ruthenium(II) complexes containing ligands of these types [24,25], one of which features in a pH-triggered assembly-disassembly process [26].…”

Section: Introductionsupporting

confidence: 56%

Ruthenium complexes of 3-hydroxy-4-pyranones and of 3-hydroxy-4-pyridinones

Burgess

Parsons

Singh

et al. 2008

Transition Met Chem

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Reactions of hydrated ruthenium chloride with 2-methyl-3-hydroxy-4-pyranone, ethylmaltol (etmaltH) and with 1,2-dimethyl-3-hydroxy-4-pyridinone (dmppH) are described. The former results in the formation of Ru(etmalt) 3 , but the course of the latter depends on conditions, producing the earlier-characterised Ru(dmmp) 3 Cl in ethanol-water solution, Ru(dmmp) 3 in aqueous solution under mild conditions, and Ru(dmpp) 2 (H 2 O) 2 after extended refluxing. EXAFS studies established ruthenium-oxygen distances in Ru(etmalt) 3 and in Ru(dmmp) 3 Á 6H 2 O. Solubilities of Ru(dmmp) 3 in methanol-water mixtures reveal greater solubility in methanol than in water, and indications of a modest solubility maximum, and thus synergic solvation, in methanol-rich mixtures.

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Section: Introductionsupporting

confidence: 56%

Ruthenium complexes of 3-hydroxy-4-pyranones and of 3-hydroxy-4-pyridinones

Burgess

Parsons

Singh

et al. 2008

Transition Met Chem

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“…In addition, the nitrogen-containing heterocycle can be further functionalized. Severin and co-workers exploited the tendency to form coordination compounds and were the first to synthesize Ru II (arene) complexes with 4-pyridonato ligands [154] yielding triangular supramolecular metallocycles [155]. A similar self-assembly was observed for 2-pyridones featuring the structural motif of 12-crown-3 with selectivity for lithium ions (Fig.…”

Section: From Pyridone-based Supramolecular Biosensors To Polynuclearmentioning

confidence: 82%

Pyrone derivatives and metals: From natural products to metal-based drugs

Kandioller

Kurzwernhart

Hanif

et al. 2011

Journal of Organometallic Chemistry

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“…[38] Ligands 1 a-h were converted with bis[dichlorido(h 6 -p-cyA C H T U N G T R E N N U N G mene)ruthenium(II)] under alkaline conditions into the corresponding Ru II complexes 2 a-h in good yields (61-85 %) (Scheme 1). [39] The reaction was performed with a slight excess of ligand to facilitate the purification step.…”

Section: Resultsmentioning

confidence: 99%

“…Similar behavior was also observed in the 13 C NMR spectra, in accord with related Ru II -arene complexes. [39] In the 1 H NMR spectrum of 2 e in CDCl 3 , two doublets with a coupling constant of 17 Hz were observed, which were assigned to the protons of the CH 2 group (see the Supporting Information). This geminal splitting can be explained by the formation of an intramolecular hydrogen bond between the hydroxymethyl moiety and the coordinated O3 atom.…”

Section: Resultsmentioning

confidence: 99%

Maltol‐Derived Ruthenium–Cymene Complexes with Tumor Inhibiting Properties: The Impact of Ligand–Metal Bond Stability on Anticancer Activity In Vitro

Kandioller

Hartinger

Nazarov

et al. 2009

Chemistry A European J

117

104

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Organometallic ruthenium-arene compounds bearing a maltol ligand have been shown to be nearly inactive in in vitro anticancer assays, presumably due to the formation of dimeric Ru(II) species in aqueous solutions. In an attempt to stabilize such complexes, [Ru(eta(6)-p-cymene)(XY)Cl] (XY=pyrones or thiopyrones) complexes with different substitution pattern of the (thio)pyrone ligands have been synthesized, their structures characterized spectroscopically, and their aquation behavior investigated as well as their tumor-inhibiting potency. The aquation behavior of pyrone systems with electron-donating substituents and of thiopyrone complexes was found to be significantly different from that of the maltol-type complex reported previously. However, the formation of the dimer can be excluded as the primary reason for the inactivity of the complex because some of the stable compounds are not active in cancer cell lines either. In contrast, studies of their reactivity towards amino acids demonstrate different reactivities of the pyrone and thiopyrone complexes, and the higher stability of the latter probably renders them active against human tumor cells.

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Halfsandwich complexes of ruthenium(II), rhodium(III) and iridium(III) with N-substituted 3-hydroxy-2-methyl-4-pyridone ligands

Cited by 33 publications

References 35 publications

Ruthenium complexes of 3-hydroxy-4-pyranones and of 3-hydroxy-4-pyridinones

Ruthenium complexes of 3-hydroxy-4-pyranones and of 3-hydroxy-4-pyridinones

Pyrone derivatives and metals: From natural products to metal-based drugs

Maltol‐Derived Ruthenium–Cymene Complexes with Tumor Inhibiting Properties: The Impact of Ligand–Metal Bond Stability on Anticancer Activity In Vitro

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