Design, synthesis and evaluation of the antioxidant and neuroprotective properties of alkyl- and terpenylphenolchlorin conjugates

Chukicheva, I. Yu.; Буравлев, Е. В.; Белых, Д. В.; Khudyaeva, I. S.; Федорова, И. В.; Шевченко, О. Г.; Maximova, Marina A; Зайнуллина, Л. Ф.; Vakhitova, Yu. V.; Kutchin, A. V.

doi:10.1007/s11172-018-2109-4

Cited by 4 publications

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“…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 on the periphery of the macrocycle exhibit AOA and RSA and these properties are in all cases due to the presence of the phenol fragment in the molecule for all types of porphyrin [ 9 , 13 , 14 , 15 , 16 ]. In this connection, the information about the porphyrin macrocycle effect on the phenolic hydroxyl groups reactivity in the interaction with free radicals is of a great interest for the design of such hybrid AO molecules.…”

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confidence: 99%

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

et al. 2018

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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.

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