Antiradical Activity of Porphyrins with a Diisobornylphenol Fragment at the Macrocycle Periphery.

Dmitrii Belykh,Nataliya Sheludchenko,Irina Chukicheva,Irina Khudyaeva,Olga Shchukina,Tatyana Rocheva,Evgeny Buravlev,Lidiya Mazaletskaya

doi:10.3390/molecules23071718

Abstract

This article focuses on the antiradical activity of a number of 2,6-diisobornylphenol-porphyrin conjugates with various spacers between the porphyrin and phenolic fragments in the model reaction of ethylbenzene oxidation initiated by azoisobutyric acid dinitrile. The study has shown that the electronic effects of the groups directly related to the 2,6-diisobornylphenol fragment exert the predominant influence both on the reactivity of the phenolic hydroxyl group in interaction with free radicals and on the antiradical activity of the molecule as a whole. The antiradical activity of the molecule is generally less affected by the nature of the substituents in the porphyrin macrocycle, mainly due to a change in the stoichiometric inhibition coefficient in the presence of relatively easily oxidizable groups. It was found that the length of the spacer between the porphyrin and phenolic fragments does not affect the antiradical activity of the conjugate.

Highlights

Hybrid antioxidants (AO) with radical scavenging activity (RSA) are known as promising compounds for the development of new biologically active substances
We investigate the RSA of natural and synthetic porphyrins containing 2,6-diisobornylphenol fragment differing in the structure of the macrocycle as well as the location and mode of conjugation
The synthesisofof target compounds is shown in Scheme

Summary

Introduction

Hybrid antioxidants (AO) with radical scavenging activity (RSA) are known as promising compounds for the development of new biologically active substances. Such hybrid molecules can combine several reaction centers capable of inhibiting oxidative processes by various mechanisms and exhibiting an intramolecular synergistic effect [1,2,3]. Is a compound with a wide spectrum of biological activity, while the effects it exhibits in most cases are associated with its antioxidant properties [4,5,6]. The insertion of fragments of molecules having their own antioxidant activity (AOA) to the periphery of the porphyrin macrocycle can have a significant effect on the AOA molecule as a whole. We have previously shown that symmetrically substituted tetra(meso-aryl)porphyrins as well as derivatives of chlorophyll a with 2,6-diisobornylphenol fragments

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Results

Conclusion