Cyclopentadienyl ruthenium complexes with naphthalene and other polycyclic aromatic ligands

Perekalin, Dmitry S.; Kudinov, Alexander R.

doi:10.1016/j.ccr.2014.06.017

Cited by 39 publications

(28 citation statements)

References 135 publications

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“…[6][7][8]27 For instance, the {(η 6 -arene)Ru} (arene = cyclopentadienyl, benzene, p-cymene, biphenyl, etc.) units can coordinate with ethylenediamine, imidazole, 2-(aminomethyl)pyridine, derived enzyme inhibitors to get a series of novel complexes with diverse biological activity and improved antitumour activity, 24,[28][29][30][31][32][33] indicating the possibility of organometallic ruthenium(II) arene complexes for the development of multi-functional antitumour drugs.…”

Section: Introductionmentioning

confidence: 99%

Discovery of a dual-targeting organometallic ruthenium complex with high activity inducing early stage apoptosis of cancer cells

Zhang

Zhao

et al. 2015

Metallomics

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Ruthenium based complexes are promising antitumour candidates due to their lower toxicity and better water-solubility compared to the platinum antitumour complexes. An epidermal growth factor receptor (EGFR) has been found to be overexpressed in a large set of tumour cells. In this work, a series of organoruthenium complexes containing EGFR-inhibiting 4-anilinoquinazoline pharmacophores were synthesised and characterised. These complexes exhibited excellent inhibitory activity against EGFR and high affinity to interact with DNA via minor groove binding, featuring dual-targeting properties. In vitro screening demonstrated that the as-prepared ruthenium complexes are anti-proliferating towards a series of cancer cell lines, in particular the non-small-cell lung cancer cell line A549. Fluorescence-activated cell sorting analysis and fluorescence microscopy revealed that the most active complex 3 induced much more early-stage cell apoptosis than its cytotoxic arene ruthenium analogue and the EGFR-inhibiting 4-anilinoquinazolines, verifying the synergetic effect of the two mono-functional pharmacophores.

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Section: Introductionmentioning

confidence: 99%

Discovery of a dual-targeting organometallic ruthenium complex with high activity inducing early stage apoptosis of cancer cells

Zhang

Zhao

et al. 2015

Metallomics

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“…Thus, naphthalene substitution in 2 by arenes, phosphines, acetonitrile, amines takes place under mild conditions and can be accelerated by visible light. [20,22,[25][26][27][28][29][30][31][32] The microwave-mediated substitution of Cp for an arene ligand was extended to the preparation of a number of CpRu(arene) + complexes (Scheme 3).…”

Section: Resultsmentioning

confidence: 99%

Microwave‐Assisted Synthesis and Transformations of Cationic CpRu(II)(naphthalene) and CpRu(II)(naphthoquinone) Complexes

Bocekova‐Gajdošíkova

Epik

Chou

et al. 2019

Helvetica Chimica Acta

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Details of the direct synthesis of cationic Ru(II)(η5‐Cp)(η6‐arene) complexes from ruthenocene using microwave heating are reported. Developed for the important catalyst precursor [Ru(II)(η5‐Cp)(η6‐1‐4,4a,8a‐naphthalene)][PF6] reaction time could be shortened from three days to 15 min. The method was extended to [Ru(II)(η6‐benzene)(η5‐Cp)][PF6], [Ru(II)(η5‐Cp)(η6‐toluene)][PF6], [Ru(II)(η5‐Cp)(η6‐mesitylene)][PF6], [Ru(II)(η5‐Cp)(η6‐hexamethylbenzene)][PF6], [Ru(II)(η5Cp)(η6‐indane)][PF6], [Ru(II)(η5‐Cp)(η6‐2,6‐dimethylnaphthalene)][PF6], and [Ru(II)(η5‐Cp)(η6‐pyrene)][PF6]. 1‐methylnaphthalene and 2,3‐dimethylnaphthalene afforded mixtures of regioisomeric complexes. [Ru(Cp)(CH3CN)3][PF6], derived from the naphthalene precursor provided access to the cationic RuCp complexes of naphthoquinone, tetralindione, 1,4‐dihydroxynaphthalene, and 1,4‐dimethoxynaphthalene. Reduction of the tetralindione complex afforded selectively the endo,endo diol derivative. X‐Ray structures of five complexes are reported.

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“…2). [6][7][8] Diruthenium cations anti-[Cp*Ru-(μ-η 6 :η 6 -L)RuCp*] x (L-O, x = 1+ or 2+, L = anthracene [L], phenanthrene [M], pyrene [N] and chrysene [O]) were reported by the groups of Kölle and Román. 7a-c A single crystal X-ray diffraction study of the chrysene complex revealed the anti-facial configuration of the metal centers.…”

Section: Introductionmentioning

confidence: 99%

“…7a-c A single crystal X-ray diffraction study of the chrysene complex revealed the anti-facial configuration of the metal centers. 7c The μ-η 6 :η 4 -naphthalene diruthenium complex [(η 4 -cod)Ru(μ-η 6 :η 4 -C 10 H 8 )Ru(η 4 -cod)(L)] (P, cod = 1,5-cyclooctadiene, L = PMe 3 , PEt 3 , and P(OMe) 3 ) reported by Bennett and co-workers also displays an anti-facial structure, 9 while Chin and co-workers recently described the syn-facial naphthalene and anthracene-bridged complexes Q and R 2+ (Fig. 2).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, electronic structure and redox properties of the diruthenium sandwich complexes [CpRu(μ-C₁₀H₈)RuCp]^x (x = 0, 1+; Cp* = C₅Me₅; C₁₀H₈ = naphthalene)

et al. 2018

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The dinuclear ruthenium complex [Cp*Ru(μ-C10H8)RuCp*] (1; Cp* = η5-C5Me5) was prepared by reduction of the cationic precursor [Cp*Ru(η6-C10H8)]PF6 with KC8. Diamagnetic 1 has a symmetric molecular structure with an anti-facial configuration of the Cp*Ru moieties coordinating to naphthalene. Density Functional Theory (DFT) studies showed an electronic structure similar to that of the analogous diiron complex [Cp*Fe(μ-C10H8)FeCp*]. Cyclic voltammetry and UV-vis spectroelectrochemistry showed that 1 can be reversibly oxidized to 1+ and 12+. Chemical oxidation with [Cp2Fe]BArF4 afforded the paramagnetic compound [1]BArF4, which was investigated by EPR, single-crystal X-ray diffractometry and DFT calculations. Reaction of 1 with Brookhart's acid gave the hydride complex [3]BArF4, which was characterized spectroscopically and crystallographically. Cyclic voltammetry showed that [3]+ is converted back to 1 upon reduction and oxidation.

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Cyclopentadienyl ruthenium complexes with naphthalene and other polycyclic aromatic ligands

Cited by 39 publications

References 135 publications

Discovery of a dual-targeting organometallic ruthenium complex with high activity inducing early stage apoptosis of cancer cells

Discovery of a dual-targeting organometallic ruthenium complex with high activity inducing early stage apoptosis of cancer cells

Microwave‐Assisted Synthesis and Transformations of Cationic CpRu(II)(naphthalene) and CpRu(II)(naphthoquinone) Complexes

Synthesis, electronic structure and redox properties of the diruthenium sandwich complexes [CpRu(μ-C₁₀H₈)RuCp]^x (x = 0, 1+; Cp* = C₅Me₅; C₁₀H₈ = naphthalene)

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Cyclopentadienyl ruthenium complexes with naphthalene and other polycyclic aromatic ligands

Cited by 39 publications

References 135 publications

Discovery of a dual-targeting organometallic ruthenium complex with high activity inducing early stage apoptosis of cancer cells

Discovery of a dual-targeting organometallic ruthenium complex with high activity inducing early stage apoptosis of cancer cells

Microwave‐Assisted Synthesis and Transformations of Cationic CpRu(II)(naphthalene) and CpRu(II)(naphthoquinone) Complexes

Synthesis, electronic structure and redox properties of the diruthenium sandwich complexes [Cp*Ru(μ-C10H8)RuCp*]x (x = 0, 1+; Cp* = C5Me5; C10H8 = naphthalene)

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Synthesis, electronic structure and redox properties of the diruthenium sandwich complexes [CpRu(μ-C₁₀H₈)RuCp]^x (x = 0, 1+; Cp* = C₅Me₅; C₁₀H₈ = naphthalene)