Novel ferrocenyl nitroxides: Synthesis, structures, electrochemistry and antioxidative activity

Qiu, Xunlin; Zhao, Hongli; Lan, Minbo

doi:10.1016/j.jorganchem.2009.08.012

Cited by 14 publications

(10 citation statements)

References 30 publications

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“…A series of ferrocenes containig nitroxyl radical (2,2,6,6-tetramethyl-piperidin-oxyl) attached to the cyclopentadienyl ring by carboxy-or amido-linkers were synthesized (Scheme 5) and their activities in scavenging superoxide radical-anion and hydroxyl radical were evaluated [46]. Results of electrochemical and UV-vis spectral study show the dependence of redox characteristics and antioxidative activity on the nature of a linker.…”

Section: Methodsmentioning

confidence: 99%

Metal-Based Antioxidants - Potential Therapeutic Candidates for Prevention the Oxidative Stress - Related Carcinogenesis: Mini-Review

Милаева¹

2011

CTMC

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The oxidative stress that is associated with the abnormal level of reactive oxygen species (ROS) is considered to be involved in the carcinogenesis process. The antioxidative defense system in the living organism regulates the toxic impact of ROS and there is strong evidence that the antioxidants prevent carcinogenesis. This review will focus on a novel approach to design synthetic metal-based antioxidants and to study their in vitro, ex vivo and in vivo activities in the cellular oxidation processes that might be involved in promotion of carcinogenesis. The antioxidants are divided into several groups depending on the nature of the ligands used: 2,6-dialkylphenols, flavonoids, polyphenols, peptides, purines, pyridines and their derivatives. Some currently achieved results in testing metal complexes as antioxidants show that they could potentially facilitate the scavenging of excess ROS, and thus restore redox balance in the damaged cells and organs. Therefore there is a strong need of the design of novel potential therapeutic candidates for prevention the oxidative stress-related carcinogenesis based on metal complexes.

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Section: Methodsmentioning

confidence: 99%

Metal-Based Antioxidants - Potential Therapeutic Candidates for Prevention the Oxidative Stress - Related Carcinogenesis: Mini-Review

Милаева¹

2011

CTMC

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“…The antioxidant activity, protection of the DNA against the oxidation damage, inhibition of lipid peroxidation process were observed for ferrocene compounds with ancillary redox active moiety (nitroxide radical, phenolic group). [62] The ability of hydroxyl-containing Schiff bases to scavenge radicals was earlier established. [48,63] On the example of Schiff bases with ferrocenyl group antioxidant effect has shown in the reaction of DNA with initiator (AAPH).…”

Section: Aaph Induced Glutathione Depletionmentioning

confidence: 99%

Electrochemical transformations and evaluation of antioxidant activity of some Schiff bases containing ferrocenyl and (thio‐)phenol, catechol fragments

Smolyaninov

Poddel’sky

Baryshnikova

et al. 2017

Applied Organom Chemis

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Electrochemical transformations and antioxidant activity of some Schiff bases 1–5 containing ferrocenyl group and (thio‐)phenol, catechol fragments were investigated. Compounds under investigation are: 2‐(ferrocenylmethylene)amino)phenol (1), 2‐((ferrocenylmethylene)amino)‐4,6‐di‐tert‐butylphenol (2), 2‐((ferrocenylmethylene)amino)‐thiophenol (3), 3‐((ferrocenylmethylene)hydrazonomethyl)‐4,6‐di‐tert‐butylcatechol (4) and 2‐((3,5‐di‐tert‐butyl‐4‐hydroxybenzylidene)amino)thiophenol (5). In a case of compounds 1–3 it has shown that the sequence of electrochemical transformations leads to the products of intramolecular cyclization – 2‐ferrocenylbenzoxazole (benzothiazole). o‐Quinone formation occurs during the electrochemical oxidation of catechol‐ferrocene 4 at the first anode stage. Electrochemical oxidation of the redox‐active fragments in Schiff bases 1–4 can be achieved indirectly at a lower potential corresponding to the oxidation of ferrocenyl moiety, consequently these substances can reveal more pronounced antioxidant properties. The antioxidant activities of the compounds were evaluated using 2,2′‐diphenyl‐1‐picrylhydrazyl radical (DPPH) assay, the reaction of 2,2′‐azobis(2‐amidinopropane hydrochloride) (AAPH) induced glutathione depletion (GSH), the oxidative damage of the DNA, the process of lipid peroxidation of rat (Wistar) brain homogenates in vitro. The compounds 1–4 in the antioxidant assays show effectiveness comparable with standard antioxidants (vitamin E, Trolox) and in some parameters superior to them. In the reaction of AAPH with the glutathione compounds 2–5 have a more pronounced protective activity than Trolox. Compounds 1–5 inhibit AAPH induced oxidation damage of the DNA. The more effective inhibitors of the lipid peroxidation process in vitro are molecules containing the bulky tert‐butyl groups: 2 and 4 and Schiff base 3.

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“…All derivatives exert a cytotoxic effect on this cell line. These compounds are more cytotoxic in vitro than the clinically employed anticancer drug carboplatin . Compounds 113 – 118 displayed improved bioactivity in comparison to the corresponding N ‐(ferrocenyl)benzoyl dipeptide ethyl esters.…”

Section: Applicationsmentioning

confidence: 99%

“…In addition to amide ester derivatives, some other ferrocenyl derivatives exhibited cytotoxic activity. Qiu et al focused their research on the synthesis of nitro derivatives, and prepared a series of ligands and coordinated them with the ferrocene moiety . Several of these complexes display significant cytotoxic activity against cancer cells.…”

Section: Applicationsmentioning

confidence: 99%

“…These compounds are more cytotoxic in vitro than the clinically employed anticancer drug carboplatin. [112] Compounds 113-118 displayed improved bioactivity in comparison to the corresponding N-(ferrocenyl)benzoyl dipeptide ethyl esters. For the N-(6-ferrocenyl-2-naphthoyl) derivatives, this simple variation in the peptide chain doubles the cytotoxic effect.…”

Section: Medicinal Applicationsmentioning

confidence: 99%

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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

128

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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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Novel ferrocenyl nitroxides: Synthesis, structures, electrochemistry and antioxidative activity

Cited by 14 publications

References 30 publications

Metal-Based Antioxidants - Potential Therapeutic Candidates for Prevention the Oxidative Stress - Related Carcinogenesis: Mini-Review

Metal-Based Antioxidants - Potential Therapeutic Candidates for Prevention the Oxidative Stress - Related Carcinogenesis: Mini-Review

Electrochemical transformations and evaluation of antioxidant activity of some Schiff bases containing ferrocenyl and (thio‐)phenol, catechol fragments

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

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