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Keywords:

  • arenes;
  • cancer;
  • cyclopentadienyl ligands;
  • organometallic;
  • ruthenium

Abstract

A structurally diverse range of lipophilic, cationic η6-arene η5-cyclopentadienyl (η5-Cp*) full-sandwich complexes of ruthenium(II) have been prepared and structurally characterized by Fourier-transform IR and NMR spectroscopy, electrospray mass spectrometry, and elemental microanalyses. Computational experiments incorporating the Hartree–Fock theory and the second-order Møller–Plesset perturbation theory predict each complex to possess a uniform δ+ electrostatic potential, with the cationic charge of the [RuCp*]+ moiety completely delocalizing throughout the molecular structure of each metallocene. In vitro cytotoxicity studies demonstrate these delocalized lipophilic cations to be potent growth inhibitors of eleven unique tumorigenic cell lines, while exhibiting significantly lower levels of toxicity towards both a normal human fibroblast and a mouse macrophage cell line. Single-crystal X-ray structural determinations are additionally reported for five complexes, [Ru(η6-C6H5(CH2)2CH3)(η5-C5(CH3)5)]BPh4, [Ru(η6-C6H5CO2CH2CH3)(η5-C5(CH3)5)]BF4, [Ru(η6-C10H8)(η5-C5(CH3)5)]BPh4, [Ru(η6-C14H10)(η5-C5(CH3)5)]BPh4, and [Ru(η6-C16H10)(η5-C5(CH3)5)]BPh4.

Featured Compounds

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  1. 1 - 13
Compound 1
Molecular Weight:633.63
Molecular Formula:C40H41BRu
InChIKey:COOXYIPJYOPGKV-UHFFFAOYSA-N
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Compound 2
Molecular Weight:647.66
Molecular Formula:C41H43BRu
InChIKey:HNLQWMRPVWLPCP-UHFFFAOYSA-N
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Compound 3
Molecular Weight:661.69
Molecular Formula:C42H45BRu
InChIKey:KABIMIOEUNHFQJ-UHFFFAOYSA-N
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Compound 4
Molecular Weight:675.71
Molecular Formula:C43H47BRu
InChIKey:RQMXUSZLMYXPMX-UHFFFAOYSA-N
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Compound 5
Molecular Weight:705.7
Molecular Formula:C43H45BO2Ru
InChIKey:VRNRTMNZKKIWNS-UHFFFAOYSA-N
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Compound 5a
Molecular Weight:473.28
Molecular Formula:C19H25BF4O2Ru
InChIKey:OUUCTAYVOHPZLP-UHFFFAOYSA-N
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Compound 6
Molecular Weight:719.72
Molecular Formula:C44H47BO2Ru
InChIKey:POPGEMRQCLAQAE-UHFFFAOYSA-N
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Compound 7
Molecular Weight:689.7
Molecular Formula:C43H45BORu
InChIKey:DZWZHTDMEGOAKD-UHFFFAOYSA-N
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Compound 8
Molecular Weight:703.72
Molecular Formula:C44H47BORu
InChIKey:HULKDZCEURUUQN-UHFFFAOYSA-N
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Compound 9
Molecular Weight:648.65
Molecular Formula:C40H42BNRu
InChIKey:NNIMWBQHKMPTHT-UHFFFAOYSA-N
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Compound 10
Molecular Weight:683.69
Molecular Formula:C44H43BRu
InChIKey:XRUPDDNUOISCFN-UHFFFAOYSA-N
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Compound 11
Molecular Weight:733.75
Molecular Formula:C48H45BRu
InChIKey:XZXJBMIEFVYQGS-UHFFFAOYSA-N
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Compound 12
Molecular Weight:757.77
Molecular Formula:C50H45BRu
InChIKey:YYOVJNSRKKMMBB-UHFFFAOYSA-N
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  1. 1 - 13