Ferrocenylvinyl-flavones: Synthesis, structure, anticancer and antibacterial activity studies

Kowalski, Konrad; Koceva‐Chyła, Aneta; Szczupak, Łukasz; Hikisz, Paweł; Bernasińska, Joanna; Rajnisz, Aleksandra; Solecka, Jolanta; Therrien, Bruno

doi:10.1016/j.jorganchem.2013.05.009

Cited by 39 publications

(21 citation statements)

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“…Ferrocene,[ Cp 2 Fe]( Cp = h 5 -C 5 H 5 ), and its derivatives belong to the most frequently used compounds in organometallic chemistry,f or example,f or catalysis [1] and bioorganometallic [2] purposes.A s[ Cp 2 Fe]i sr edox-active,i th as also been applied in redox-switchable systems [3] or as ar eference in cyclic voltammetry.W hile the oxidation of [Cp 2 Fe]t o [Cp 2 Fe] + is as imple reversible one-electron process,a nd its reduction goes along with as tructural change,t he electrochemical oxidation and reduction of the isolobal derivative [Cp*Fe(h 5 -P 5 )] (Cp* = h 5 -C 5 Me 5 )a re more complex. [4] Here, [Cp*Fe(h 5 -P 5 )] is either oxidized or reduced to [Cp*FeP 5 ] + (17 valence electrons (VE)) or [Cp*FeP 5 ] À (19 VE), followed by immediate dimerization to [(Cp*FeP 5 ) 2 ] 2+ or [(Cp*FeP 5 ) 2 ] 2À ,r espectively.R ecently,b oth species as well as the doubly reduced dianion [Cp*Fe(h 4 -P 5 )] 2À have been isolated and characterized by using KH or Kasthe reducing agent.…”

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Arsenic‐Rich Polyarsenides Stabilized by Cp*Fe Fragments

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The redox chemistry of [Cp*Fe(η -As )] (1, Cp*=η -C Me ) has been investigated by cyclic voltammetry, revealing a redox behavior similar to that of its lighter congener [Cp*Fe(η -P )]. However, the subsequent chemical reduction of 1 by KH led to the formation of a mixture of novel As scaffolds with n up to 18 that are stabilized only by [Cp*Fe] fragments. These include the arsenic-poor triple-decker complex [K(dme) ][{Cp*Fe(μ,η -As )} ] (2) and the arsenic-rich complexes [K(dme) ] [(Cp*Fe) (μ,η -As )] (3), [K(dme) ] [(Cp*Fe) (μ,η -As )] (4), and [K(dme) ] [(Cp*Fe) (μ ,η -As )] (5). Compound 4 and the polyarsenide complex 5 are the largest anionic As ligand complexes reported thus far. Complexes 2-5 were characterized by single-crystal X-ray diffraction, H NMR spectroscopy, EPR spectroscopy (2), and mass spectrometry. Furthermore, DFT calculations showed that the intermediate [Cp*Fe(η -As )] , which is presumably formed first, undergoes fast dimerization to the dianion [(Cp*Fe) (μ,η -As )] .

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Arsenic‐Rich Polyarsenides Stabilized by Cp*Fe Fragments

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“…Ferrocen [Cp 2 Fe]( Cp = h 5 -C 5 H 5 )u nd seine Derivate gehçren zu den am meisten verwendeten Verbindungen in der metallorganischen Chemie,z .B.f ürd ie Katalyse [1] oder für biometallorganische Zwecke. [2] Da [Cp 2 Fe]r edoxaktiv ist, wird es auch in schaltbaren Redoxsystemen [3] oder als Referenz bei der Cyclovoltammetrie genutzt. Während es sich bei der Oxidation von [Cp 2 Fe]nach [Cp 2 Fe] + um einen einfachen reversiblen Ein-Elektronen-Prozess handelt und die Reduktion mit einer Strukturänderung einhergeht, sind die elektrochemische Oxidation und Reduktion des isolobalen Deri-vats [Cp*Fe(h 5 -P 5 )] (Cp* = h 5 -C 5 Me 5 )komplexer.…”

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“…[2] Da [Cp 2 Fe]r edoxaktiv ist, wird es auch in schaltbaren Redoxsystemen [3] oder als Referenz bei der Cyclovoltammetrie genutzt. Während es sich bei der Oxidation von [Cp 2 Fe]nach [Cp 2 Fe] + um einen einfachen reversiblen Ein-Elektronen-Prozess handelt und die Reduktion mit einer Strukturänderung einhergeht, sind die elektrochemische Oxidation und Reduktion des isolobalen Deri-vats [Cp*Fe(h 5 -P 5 )] (Cp* = h 5 -C 5 Me 5 )komplexer. [4] Hier wird [Cp*Fe(h 5 -P 5 )] entweder zu [Cp*FeP 5 ] + (17 Va lenzelektronen (VE)) oder zu [Cp*FeP 5 ] À (19 VE) oxidiert oder reduziert, und anschließend erfolgt eine sofortige Dimerisierung zu [(Cp*FeP 5 ) 2 ] 2+ bzw.…”

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Durch Cp*Fe‐Fragmente stabilisierte, Arsen‐reiche Polyarsenide

et al. 2017

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Die Untersuchung der Redoxchemie von [Cp*Fe(h 5 -As 5 )] (1)( Cp* = h 5 -C 5 Me 5 )m ittels Cyclovoltammetrie ergab ein Redoxverhalten, das jenem des leichteren Verwandten [Cp*Fe(h 5 -P 5 )] ähnelt. Die anschließende chemische Reduktion von 1 durch KH führt zur Bildung eines Gemisches von Produkten mit neuartigen As n -Gerüsten (n = bis zu 18), die lediglich durch[ Cp*Fe]-Fragmente stabilisiert werden. Dazu gehçren der Arsen-arme Tripeldeckerkomplex [K(dme) 2 ]-[{Cp*Fe(m,h 2:2 -As 2 )} 2 ]( 2)u nd die Arsen-reichen Komplexe [K(dme) 3 ] 2 [(Cp*Fe) 2 (m,h 4:4 -As 10

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“…The Pd‐catalyzed phosphine‐free Heck cross‐coupling reaction of vinylferrocene 16 with bromochromones 17 for the synthesis of ferrocenylvinyl–flavone 18 (Scheme ) under solid–liquid phase‐transfer conditions (potassium carbonate or sodium carbonate/tetrabutylammonium bromide) was described by Konrad et al The resulting flavones were obtained in fair yields and exhibited good cytotoxic and antibacterial activities …”

Section: Methods Of Synthesis Of Ferrocene Derivativesmentioning

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Recent advances in the synthesis, biological activities and various applications of ferrocene derivatives

Larik

Saeed

Fattah

et al. 2016

Applied Organom Chemis

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Ferrocene derivatives constitute an important class of organometallic compounds with not only an extensive range of biological activities but also diverse industrial as well as material science applications. These stimulating features of ferrocene derivatives spurred us to review the recent advances in synthesis methods and biological and other applications reported in the latest literature. An effort has been made to summarize the recent developments in synthetic methods providing access to ferrocene scaffolds and the useful medicinal and material applications, including agricultural, catalytic, polymer, conducting, redox mediating, ferrocenyl stationary phase, rocket propellant and ion sensing applications. Ferrocene‐based bulky metallocenes are also discussed.

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Ferrocenylvinyl-flavones: Synthesis, structure, anticancer and antibacterial activity studies

Cited by 39 publications

References 56 publications

Arsenic‐Rich Polyarsenides Stabilized by Cp*Fe Fragments

Arsenic‐Rich Polyarsenides Stabilized by Cp*Fe Fragments

Durch Cp*Fe‐Fragmente stabilisierte, Arsen‐reiche Polyarsenide

Recent advances in the synthesis, biological activities and various applications of ferrocene derivatives

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