Synthesis, characterization and in vitro anti-cancer activity of N-(ferrocenyl)benzoyl tri- and tetrapeptide esters

Corry, Alan J.; Mooney, Áine; O'sullivan, Dermot A.; Kenny, Peter T.M.

doi:10.1016/j.ica.2009.01.021

Cited by 23 publications

(16 citation statements)

References 32 publications

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“…Cancer is a set of diseases in which the affected cells display the following abnormalities: (i) uncontrolled growth and division beyond what is normal, (ii) invasion and destruction of neighbouring cells and (iii) metastasis, i.e. the spreading of the disease to other locations . The biochemistry of cancer is enormously complex, but one cause that has been generally accepted is that reactive oxygen species play many important roles in carcinogenesis and the progression of tumours.…”

Section: Resultsmentioning

confidence: 99%

Magnetic NiFe₂O₄ nanoparticles: efficient, heterogeneous and reusable catalyst for synthesis of acetylferrocene chalcones and their anti‐tumour activity

Abu‐Dief

Nassar

Elsayed

2016

Applied Organom Chemis

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A robust synthesis of magnetic NiFe 2 O 4 nanoparticles via a hydrothermal technique was investigated. The prepared magnetic NiFe 2 O 4 nanoparticles were characterized using powder X-ray diffraction (XRD), scanning electron microscopy, transmission electron microscopy (TEM), high-resolution TEM, energy-dispersive X-ray spectroscopy, thermogravimetric analysis, infrared spectroscopy and vibrating sample magnetometry. XRD and TEM analyses confirmed the formation of single-phase ultrafine nickel ferrite nanoparticles with highly homogeneous cubic shape and elemental composition. Moreover, the prepared magnetic NiFe 2 O 4 nanoparticles were used as an efficient, cheap and eco-friendly catalyst for the Claisen-Schmidt condensation reaction between acetylferrocene and various aldehydes (aromatic and/or heterocyclic) yielding acetylferrocene chalcones in excellent yields, with easy work-up and reduced reaction time. The products were purified via crystallization. The structures of the produced compounds were elucidated using various spectroscopic analyses ( 1 H NMR, 13 C NMR, GC-MS). The catalyst is readily recovered by simple magnetic decantation and can be recycled several times with no discernible loss of catalytic activity. Furthermore, the prepared chalcone derivatives were evaluated for their anti-tumour activity against three human tumour cell lines, namely HCT116 (colon cancer), MCF7 (breast cancer) and HEPG2 (liver cancer), and showed a good activity against colon cancer. Scheme 1. List of aldehyde substrates (2a-m) and chalcone products (3am) with alkyl groups. A. M. Abu-Dief et al. wileyonlinelibrary.com/journal/aoc

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Section: Resultsmentioning

confidence: 99%

Magnetic NiFe₂O₄ nanoparticles: efficient, heterogeneous and reusable catalyst for synthesis of acetylferrocene chalcones and their anti‐tumour activity

Abu‐Dief

Nassar

Elsayed

2016

Applied Organom Chemis

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“…4 O grupamento ferroceno exibe interessantes propriedades químicas e ao ser inserido em estruturas orgânicas pode produzir derivados com importantes aplicações e, além disso, apresenta baixo custo. [5][6][7] O ferroceno apresenta propriedades de oxirredução, ou seja, é capaz de sofrer oxidação reversível, ocorrendo a geração de espécie, cátion-radical como mostrado no Esquema 2. O ferroceno obedece a regra dos 18 elétrons e, desse total, 12 elétrons encontram-se em orbitais ligantes e os outros 6 em orbitais não ligantes.…”

Section: Introductionunclassified

Síntese de heterociclos bioativos derivados do ferroceno

Pereira¹,

Venzke²,

Trossini³

2013

Quím. Nova

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Recebido em 9/10/11; aceito em 1/8/12; publicado na web em 28/11/12 SYNTHESIS OF BIOACTIVE HETEROCYCLIC FERROCENE DERIVATIVES. The discovery of ferrocene marked one of the points of departure for modern organometallic chemistry. In general, the compounds of ferrocene derivatives are widely applied in several areas. One of the most important applications of ferrocene is the development of more active drugs, especially in cases where there is resistance to current drugs. Bioactive agents containing ferrocene have proven effective in combating diseases such as cancer, malaria, HIV, Alzheimer and conditions caused by fungi and bacteria. In this context, the present paper aims to highlights the synthesis of heterocycles containing ferrocene moiety and their use in medicinal chemistry.Keywords: ferrocene; drugs; heterocycles. INTRODUÇÃOO ferroceno é uma substância organometálica do tipo sanduíche e foi sintetizado, acidentalmente, por Pauson e Kealy em 1951. Na busca pela síntese do fulvaleno, Pauson e Kealy promoveram a reação do ciclopentadieno e o reagente de Grignard formando o brometo de ciclopentadienilmagnésio e, em seguida, adicionaram o cloreto férrico obtendo uma substância de coloração vermelho-alaranjado de notável estabilidade, o ferroceno (Esquema 1). 1 Entretanto, a estrutura confirmada da substância foi apresentada somente mais tarde, em duas publicações independentes: uma por Fischer e Pfab; a outra por Wilkinson, Rosenblum, Whiting e Woodward. Posteriormente, a substância foi denominada de ferroceno por Woodward.1-3 A descoberta do ferroceno impulsionou as pesquisas de compostos organometálicos.4 O grupamento ferroceno exibe interessantes propriedades químicas e ao ser inserido em estruturas orgânicas pode produzir derivados com importantes aplicações e, além disso, apresenta baixo custo.5-7 O ferroceno apresenta propriedades de oxirredução, ou seja, é capaz de sofrer oxidação reversível, ocorrendo a geração de espécie, cátion-radical como mostrado no Esquema 2. O ferroceno obedece a regra dos 18 elétrons e, desse total, 12 elétrons encontram-se em orbitais ligantes e os outros 6 em orbitais não ligantes. Os elétrons não ligantes determinam propriedades importantes do ferroceno como seu potencial redox, além de outras propriedades químicas. 8Uma das aplicações do ferroceno está baseada na sua capacidade de absorver radiação. Deste modo, um cromóforo de ferroceno confere uma coloração brilhante variando de amarelo-alaranjado a azul-esverdeado e esses produtos são firmemente fixados em vários materiais, incluindo produtos sintéticos. Tudo isso torna possível se empregar os derivados do ferroceno como corantes, materiais fotográficos e sensibilizadores de luz.9,10 Outra aplicação importante está baseada na habilidade do ferroceno e seus derivados de regular os processos de combustão, o que leva a possibilidades de uso como anti-incrustantes e agentes antidetonantes. Antibacterianos -aspectos gerais e derivados sintéticosDevido o uso indiscriminado dos antibacterianos, principalmente as penicilinas e...

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“…[16][17][18] The nature of the bridge between donor and acceptor is an active area of study. As the dipeptide derivatives were more active than amino acid derivatives, [19] here we report the synthesis, crystal structure and properties of the ferrocene-dipeptide conjugates.…”

Section: Introductionmentioning

confidence: 99%

A series of novel ferrocene‐based dipeptide receptors for electrochemistry and biological activity

Zheng

Shi

et al. 2013

Applied Organom Chemis

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Synthesis of ferrocene‐based dipeptide receptors FcL1, FcL2, FcL3, FcL4, FcL5 was carried out by the acylation reaction of ferrocenecarboxylic acid with dipeptide esters. Compounds were characterized by IR, 1H NMR, 13C NMR and elemental analysis. Single‐crystal X‐ray analysis of FcL3 showed it has two independent chiral molecules and the two chiral atoms (C12 and C35) are in R configuration. Their cyclic voltammetric behaviors showed a pair of well‐defined and stable redox waves in the potential range 0.00–1.00 V. The configuration of the metals influenced the receptor's characteristics greatly, and at the same time the FcL compounds could selectively sense group IIB metal ions Zn2+, Cd2+ and Hg2+. The biological activities of FcL1, FcL2, FcL3, FcL4, FcL5 were studied against the tested bacteria; among them, FcL4 showed significant activity against all five bacterial strains tested. Copyright © 2013 John Wiley & Sons, Ltd.

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Synthesis, characterization and in vitro anti-cancer activity of N-(ferrocenyl)benzoyl tri- and tetrapeptide esters

Cited by 23 publications

References 32 publications

Magnetic NiFe₂O₄ nanoparticles: efficient, heterogeneous and reusable catalyst for synthesis of acetylferrocene chalcones and their anti‐tumour activity

Magnetic NiFe₂O₄ nanoparticles: efficient, heterogeneous and reusable catalyst for synthesis of acetylferrocene chalcones and their anti‐tumour activity

Síntese de heterociclos bioativos derivados do ferroceno

A series of novel ferrocene‐based dipeptide receptors for electrochemistry and biological activity

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Synthesis, characterization and in vitro anti-cancer activity of N-(ferrocenyl)benzoyl tri- and tetrapeptide esters

Cited by 23 publications

References 32 publications

Magnetic NiFe2O4 nanoparticles: efficient, heterogeneous and reusable catalyst for synthesis of acetylferrocene chalcones and their anti‐tumour activity

Magnetic NiFe2O4 nanoparticles: efficient, heterogeneous and reusable catalyst for synthesis of acetylferrocene chalcones and their anti‐tumour activity

Síntese de heterociclos bioativos derivados do ferroceno

A series of novel ferrocene‐based dipeptide receptors for electrochemistry and biological activity

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Product

Resources

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Magnetic NiFe₂O₄ nanoparticles: efficient, heterogeneous and reusable catalyst for synthesis of acetylferrocene chalcones and their anti‐tumour activity

Magnetic NiFe₂O₄ nanoparticles: efficient, heterogeneous and reusable catalyst for synthesis of acetylferrocene chalcones and their anti‐tumour activity