Synthesis and Characterization of N‐Heterocyclic Carbene Dithiocarbamate Platinum Complexes with Antitumoral Activity

Verron, Raphaël; Achard, Thierry; Seguin, Cendrine; Fournel, Sylvie; Bellemin‐Laponnaz, Stéphane

doi:10.1002/ejic.202000329

Cited by 17 publications

(4 citation statements)

References 32 publications

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“…The reaction conditions were chosen based on complexation reactions recently published by Choudhury et al [6b] . and Bellemin‐Laponnaz et al [23] . The molecular structures of 6 a and 7 a are that of so‐called PEPPSI‐type complexes, which gained application as catalysts in C−C coupling reactions.…”

Section: Resultsmentioning

confidence: 99%

“…Scheme 3 also depicts the synthesis of the dinuclear iron(II)/ palladium(II) complex 6 a and the structurally analogue iron(II)/ platinum(II) complex 7 a, which is accessible from PtCl 2 /NaI in pyridine. The reaction conditions were chosen based on complexation reactions recently published by Choudhury et al [6b] and Bellemin-Laponnaz et al [23] The molecular structures of 6 a and 7 a are that of so-called PEPPSI-type complexes, which gained application as catalysts in CÀ C coupling reactions.…”

Section: Synthesesmentioning

confidence: 99%

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Transition Metal Complexes of NHC Ligands Functionalized with the Cationic (η⁵‐Cyclopentadienyl)(η⁶‐phenyl)iron(II) Motif

et al. 2022

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Starting from [(η5‐cyclopentadienyl)(η6‐phenyl)iron(II)]imidazole, dicationic imidazolium salts were prepared by N‐alkylation. Reaction of these compounds with basic metal precursors such as mesityl copper(I) or palladium(II) acetate led to mono respectively dicationic transition metal NHC complexes (NHC=N‐heterocyclic carbene). Transmetalation using the copper(I) complexes opened up the access to NHC gold(I) compounds. PEPPSI‐type NHC complexes of palladium(II) and platinum(II) were prepared by offering a neutral pyridine ligand to the transition metal center. A rhodium(I) NHC complex was accessible by deprotonation of the dicationic imidazolium precursor and subsequent treatment with [(COD)Rh(μ2‐Cl)]2 (COD=1,5‐cyclooctadiene). The new NHC complexes were investigated by means of NMR spectroscopy, mass spectrometry as well as single crystal X‐ray structure analysis. Both, the palladium(II) containing PEPPSI‐type and the gold(I) complex, were investigated for their catalytic properties in typical model reactions such as cyclization reactions, Suzuki coupling and cyanation. In addition, a selenium adduct was synthesized in order to study the electronic properties of the underlying ligand backbone. Based on the chemical shift in the 77Se NMR spectrum, it is evident that these NHC ligands possess rather poor π‐acidity.

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Section: Resultsmentioning

confidence: 99%

Section: Synthesesmentioning

confidence: 99%

Transition Metal Complexes of NHC Ligands Functionalized with the Cationic (η⁵‐Cyclopentadienyl)(η⁶‐phenyl)iron(II) Motif

et al. 2022

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“…The most relevant examples in this area are cisplatin, carboplatin, and oxaliplatin . When a NHC ligand is coordinated to a platinum center, the resulting Pt-NHC complexes have been reported to be promising anticancer agents against cisplatin-resistant tumors …”

Section: Comparing the Various Approachesmentioning

confidence: 99%

“…61 When a NHC ligand is coordinated to a platinum center, the resulting Pt-NHC complexes have been reported to be promising anticancer agents against cisplatin-resistant tumors. 62 Despite the use of Pt-NHC complexes in medicinal chemistry and catalysis, there are few reports dealing with the simple and facile synthetic assembly of the compounds. The weak base route to [Pt(NHC)(SMe 2 )Cl 2 ] complexes was first reported by Nolan in 2020 and then expanded upon in 2022, as will be discussed in a following paragraph.…”

Section: Metal-nhc Complexesmentioning

confidence: 99%

Advances in the Synthesis and Applications of N-Heterocyclic Carbene Metal Complexes with a Focus on the Weak Base Route

Scattolin,

Logvinov,

Tzouras

et al. 2023

Organometallics

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N-heterocyclic carbene (NHC) ligands have evolved from being simple lab curiosities to tertiary phosphine mimics to finally take center stage as unique supporting ligands in organometallic chemistry, homogeneous catalysis, and more recently in medicinal chemistry and materials science applications. Some of these aspects are presented here from a perspective of researchers that have been fascinated by the area for quite some time.

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Transition‐Metal‐Free C(sp²)‐H Dithiocarbamation and Chromone Annulation Cascade for 3‐Dithiocarbamyl Chromone Synthesis

et al. 2021

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The transition‐metal‐free synthesis of 3‐dithiocarbamyl chromones by reacting o‐hydroxyphenylenaminones with thiurams in the presence of KIO3 and TEMPO is reported. In addition, the 3‐dithiocarbamyl chromones synthesized herein have been successfully utilized as starting materials in the synthesis of 3‐dithiocarbamyl pyrimidines and 3‐(benzylthio)chromones via featured chromone ring opening and C−S bond cleavage, respectively.

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Synthesis and Characterization of N‐Heterocyclic Carbene Dithiocarbamate Platinum Complexes with Antitumoral Activity

Abstract: Supporting information for this article is given via a link at the end of the document.

Cited by 17 publications

References 32 publications

Transition Metal Complexes of NHC Ligands Functionalized with the Cationic (η⁵‐Cyclopentadienyl)(η⁶‐phenyl)iron(II) Motif

Transition Metal Complexes of NHC Ligands Functionalized with the Cationic (η⁵‐Cyclopentadienyl)(η⁶‐phenyl)iron(II) Motif

Advances in the Synthesis and Applications of N-Heterocyclic Carbene Metal Complexes with a Focus on the Weak Base Route

Transition‐Metal‐Free C(sp²)‐H Dithiocarbamation and Chromone Annulation Cascade for 3‐Dithiocarbamyl Chromone Synthesis

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Synthesis and Characterization of N‐Heterocyclic Carbene Dithiocarbamate Platinum Complexes with Antitumoral Activity

Abstract: Supporting information for this article is given via a link at the end of the document.

Cited by 17 publications

References 32 publications

Transition Metal Complexes of NHC Ligands Functionalized with the Cationic (η5‐Cyclopentadienyl)(η6‐phenyl)iron(II) Motif

Transition Metal Complexes of NHC Ligands Functionalized with the Cationic (η5‐Cyclopentadienyl)(η6‐phenyl)iron(II) Motif

Advances in the Synthesis and Applications of N-Heterocyclic Carbene Metal Complexes with a Focus on the Weak Base Route

Transition‐Metal‐Free C(sp2)‐H Dithiocarbamation and Chromone Annulation Cascade for 3‐Dithiocarbamyl Chromone Synthesis

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Product

Resources

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Transition Metal Complexes of NHC Ligands Functionalized with the Cationic (η⁵‐Cyclopentadienyl)(η⁶‐phenyl)iron(II) Motif

Transition Metal Complexes of NHC Ligands Functionalized with the Cationic (η⁵‐Cyclopentadienyl)(η⁶‐phenyl)iron(II) Motif

Transition‐Metal‐Free C(sp²)‐H Dithiocarbamation and Chromone Annulation Cascade for 3‐Dithiocarbamyl Chromone Synthesis