Synthesis and antioxidant activity of sterically hindered bis-pyrocatechol thioethers

Smolyaninov, I. V.; Pitikova, O. V.; Rychagova, E. S.; Корчагина, Е. О.; Poddel’sky, Andrey I.; Smolyaninova, S. A.; Берберова, Н. Т.

doi:10.1007/s11172-016-1669-4

Cited by 11 publications

(6 citation statements)

References 14 publications

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“…3,5‐Di‐ tert ‐butylcatechol demonstrates a remarkable promoting effect . The concentration of GSH decreases by 30 μM in comparison with the results obtained for AAPH.…”

Section: Resultsmentioning

confidence: 96%

“…The introduction of tert ‐butyl groups in the aromatic ring results in an insignificant decrease of EC 50 value in a case of Schiff base 2 . In general, the antiradical activity of compounds with ferrocenyl group 1–4 is comparable to the natural antioxidant α‐tocopherol . The calculation of the stoichiometric number of molecules of the neutralized radical (n DPPH ) per one molecule of the antioxidant revealed that this parameter for compounds 1–5 varies from 1.5 to 2.2.…”

Section: Resultsmentioning

confidence: 99%

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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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“…3,5‐Di‐ tert ‐butylcatechol demonstrates a remarkable promoting effect . The concentration of GSH decreases by 30 μM in comparison with the results obtained for AAPH.…”

Section: Resultsmentioning

confidence: 96%

Section: Resultsmentioning

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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“…Now the development of a new synthetic approach to obtain catechol/hydroquinone thio-ethers and the investigation of their structure and properties has become topical [ 48 , 49 , 50 , 51 , 52 ]. The Michael addition reaction of thiols to ortho -, para -benzoquinones [ 53 , 54 , 55 , 56 ] or nucleophilic substitution [ 57 , 58 ] are often applied to synthesize thio-ethers. The application of molecular iodine or diacetoxyiodo-benzene in the reactions of sulfonating agents with cyclohexanones or with masked o -benzoquinones leads to thiolated catechols [ 59 , 60 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antioxidant Activity of New Catechol Thioethers with the Methylene Linker

et al. 2022

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Novel catechol thio-ethers with different heterocyclic substituents at sulfur atom were prepared by reacting 3,5-di-tert-butyl-6-methoxymethylcatechol with functionalized thiols under acidic conditions. A common feature of compounds is a methylene bridge between the catechol ring and thioether group. Two catechols with the thio-ether group, bound directly to the catechol ring, were also considered to assess the effect of the methylene linker on the antioxidant properties. The crystal structures of thio-ethers with benzo-thiazole moieties were established by single-crystal X-ray analysis. The radical scavenging and antioxidant activities were determined using 2,2′-diphenyl-1-picrylhydrazyl radical test, ABTS∙+, CUPRAC (TEAC) assays, the reaction with superoxide radical anion generated by xanthine oxidase (NBT assay), the oxidative damage of the DNA, and the process of lipid peroxidation of rat liver (Wistar) homogenates in vitro. Most catechol-thioethers exhibit the antioxidant effect, which varies from mild to moderate depending on the model system. The dual anti/prooxidant activity characterizes compounds with adamantyl or thio-phenol substituent at the sulfur atom. Catechol thio-ethers containing heterocyclic groups (thiazole, thiazoline, benzo-thiazole, benzo-xazole) can be considered effective antioxidants with cytoprotective properties. These compounds can protect molecules of DNA and lipids from the different radical species.

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“…[ 20 , 21 , 22 , 23 , 24 , 25 ]. Catechol-thioethers are prospective objects from the viewpoint of studying the antioxidant properties of polyfunctional compounds, and are new objects in coordination chemistry [ 26 , 27 , 28 , 29 , 30 , 31 , 32 ]. For example, complexes of 4,6-di-tert-butylcatechol derivatives containing cystamine or cysteine residues at position 3 of such ligands are actively studied [ 26 , 27 ].…”

Section: Introductionmentioning

confidence: 99%

Triphenylantimony(V) Catecholates of the Type (3-RS-4,6-DBCat)SbPh3-Catechol Thioether Derivatives: Structure, Electrochemical Properties, and Antiradical Activity

et al. 2021

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A new series of triphenylantimony(V) 3-alkylthio/arylthio-substituted 4,6-di-tert-butylcatecholates of the type (3-RS-4,6-DBCat)SbPh3, where R = n-butyl (1), n-hexyl (2), n-octyl (3), cyclopentyl (4), cyclohexyl (5), benzyl (6), phenyl (7), and naphthyl-2 (8), were synthesized from the corresponding catechol thioethers and Ph3SbBr2 in the presence of a base. The crystal structures of 1, 2, 3, and 5 were determined by single-crystal X-ray analysis. The coordination polyhedron of 1–3 is better described as a tetragonal pyramid with a different degree of distortion, while that for 5- was a distorted trigonal bipyramid (τ = 0.014, 0.177, 0.26, 0.56, respectively). Complexes demonstrated different crystal packing of molecules. The electrochemical oxidation of the complexes involved the catecholate group as well as the thioether linker. The introduction of a thioether fragment into the aromatic ring of catechol ligand led to a shift in the potential of the “catechol/o-semiquinone” redox transition to the anodic region, which indicated the electron-withdrawing nature of the RS group. The radical scavenging activity of the complexes was determined in the reaction with DPPH radical.

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Synthesis and antioxidant activity of sterically hindered bis-pyrocatechol thioethers

Cited by 11 publications

References 14 publications

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

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

Synthesis and Antioxidant Activity of New Catechol Thioethers with the Methylene Linker

Triphenylantimony(V) Catecholates of the Type (3-RS-4,6-DBCat)SbPh3-Catechol Thioether Derivatives: Structure, Electrochemical Properties, and Antiradical Activity

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