Antioxidative Activity of Ferrocenes Bearing 2,6‐Di‐Tert‐Butylphenol Moieties

Abstract

The antioxidative activity of ferrocenes bearing either 2,6-di-tert-butylphenol or phenyl groups has been compared using DPPH (1,1-diphenyl-2-picrylhydrazyl) test and in the study of the in vitro impact on lipid peroxidation in rat brain homogenate and on some characteristics of rat liver mitochondria. The results of DPPH test at 20°C show that the activity depends strongly upon the presence of phenolic group but is improved by the influence of ferrocenyl fragment. The activity of N-(3,5-di-tert-butyl-4-hydroxyphenyl)iminomethylferrocene (1), for instance, was 88.4%, which was higher than the activity of a known antioxidant 2,6-di-tert-butyl-4-methylphenol (BHT) (48.5%), whereas the activity of N-phenyl-iminomethylferrocene 2 was almost negligible −2.9%. The data obtained demonstrate that the compounds with 2,6-di-tert-butylphenol moiety are significantly more active than the corresponding phenyl analogues in the in vitro study of lipid peroxidation in rat brain homogenate. Ferrocene 1 performs a promising behavior as an antioxidant and inhibits the calcium-dependent swelling of mitochondria. These results allow us to propose the potential cytoprotective (neuroprotective) effect of ditopic compounds containing antioxidant 2,6-di-tert-butylphenol group and redox active ferrocene fragment.

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

“…A promising result has been achieved [26] by the evaluation of antioxidant properties of ferrocenes bearing 2,6-ditert-butylphenol groups linked to ferrocene by containing various conjugated and non-conjugated spacers (Scheme 4).…”

“…The in vivo study has been performed for the most active compounds using fish (Asipenser gueldenstaedti B.) and Wistar rats [26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42].…”

Pharmaceutico-Analytical Comparison of Daruharidra Arka and Kvatha as Ascotana Drug

“…This property may be helpful in reducing the symptoms like Lohita netrata and Dāha of Netra Abhiṣyanda when used as Āścotana drug. 2, 6-Ditertbutylphenol-and 4-Hydroxyphenethylalcohol (thyrosol) are known to be potent antioxidants 3 which promote healing of conjunctival epithelial cells. 2-methoxy-4-(prop-1-en-1-yl)phenol and 4-hydroxyl-3-methoxyphenethanol (homovanillyl alcohol) which are aromatic compounds provide fragrance to the medicine and also these compounds are known for antioxidant properties 4 .…”

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

“…Ferrocenyl Schiff bases demonstrate different biological activity: anticancer, antifungal, radical scavenging, antioxidant activity and the DNA protection . The ability of ferrocenyl‐containing compounds to scavenge radicals is caused by the presence of redox‐active fragment with pronounced antioxidant properties such as phenol, catechol or curcumin . The electrochemical methods were shown to serve as the useful tools in research of redox properties and design of redox‐modulating agents .…”