Electrochemical transformations and anti/prooxidant activity of sterically hindered o-benzoquinones

Smolyaninov, I. V.; Kuzmin, V.V.; Arsenyev, Maxim V.; Smolyaninova, S. A.; ́sky, A. I. Poddel; Берберова, Н. Т.

doi:10.1007/s11172-017-1876-7

Cited by 18 publications

(9 citation statements)

References 60 publications

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“…The substitution of thiophenol group by mercaptobenzimidazole one provides a similar action. The antioxidant activity of 5 is in good agreement with the similar influence of the previously studied phenol ((2‐HSPh)−N=CH−Ph‐4‐OH) on the LP process (13.0±1.5 nmol mL −1 ) [8g] …”

Section: Resultssupporting

confidence: 88%

“…The previously studied 2,6‐di‐ tert ‐butyl‐4‐((2‐mercaptophenyl)iminomethyl)phenol ((2‐HSPh)−N=CH−Ph‐4‐OH) is also capable of cyclization with a formation of benzothiazoline fragment. The first oxidation potential of this compound was 0.76 V, while the second anodic peak by phenolic group was observed at a more anodic potential [8g] . In the case of compounds 3 and 4 , the E ox1 values are close to the results obtained for compounds containing a benzothiazoline group in the ortho ‐position to phenolic hydroxyl (≈1.0 V) [15] …”

Section: Resultssupporting

confidence: 78%

“…It should be noted that the transfer of the hydroxyl group to the adjacent position with CH=N bond, as thiol group from ortho ‐ to para ‐position leads to the stabilization of the one‐electron oxidized form of 5 in comparison with (2‐HSPh)−N=CH−Ph‐4‐OH [8g] . The third oxidation peak corresponds presumably to a deeper oxidation of the generated monocations.…”

Section: Resultsmentioning

confidence: 99%

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Catechol‐ and Phenol‐Containing Thio‐Schiff Bases: Synthesis, Electrochemical Properties and Biological Evaluation

et al. 2021

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A number of novel catechol-and phenol-containing Schiff bases with thiophenol or mercaptobenzimidazole groups have been synthesized. Electrochemical studies of the target compounds were carried out in order to establish the primary centres involved in redox reactions, and the mechanism of oxidative transformations. The antioxidant activities of the compounds were determined using different assays. Compounds combining the catechol group with the mercaptobenzimidazole or benzothiazoline cycles exhibit more pronounced antioxidant activity in the concerning tests. However, a significant promoting effect on the process of lipid peroxidation of rat brain homogenates was found in the presence of catechols. Antibacterial and cytotoxic effects of Schiff bases can be caused by the possibility of ROS and o-benzoquinones generation. It was established that some compounds have a moderate bacteriostatic effect against Staphylococcus aureus strains. Schiff bases with catechol and heterocyclic groups exhibit a good antiproliferative activity (IC 50 < 10 μM) towards MCF-7, HTC-116 and A549 cell lines.

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Section: Resultssupporting

confidence: 88%

Section: Resultssupporting

confidence: 78%

Section: Resultsmentioning

confidence: 99%

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Catechol‐ and Phenol‐Containing Thio‐Schiff Bases: Synthesis, Electrochemical Properties and Biological Evaluation

et al. 2021

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“…Redox-active quinoid compounds have been widely investigated as anti-cancer, anti-bacterial, anti-inflammatory, and anti-parasitic agents [ 1 , 2 , 3 , 4 , 5 , 6 ]. Such compounds demonstrate a wide spectrum of pharmacological activity [ 7 , 8 , 9 ] and behave both as antioxidants [ 10 , 11 , 12 , 13 , 14 , 15 ] and prooxidants [ 16 , 17 , 18 , 19 ]. Functionalization of o-quinones/catechols allows the expansion of their redox potential and biochemical activity as well as the modification of coordinating ability, etc.…”

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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“…Синтез и свойства галогенсодержащих макроциклических иминов антрахинона -хемосенсоров на катионы металлов вание отклика при взаимодействии с аналитом, часто используют производные хинонов, так как они являются коммерчески доступными и глубокоокрашенными соединениями [8][9][10].…”

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Synthesis and properties of halogen-containing macrocyclic anthraquinone imines – chemosensors for metal cations

Kudrevatykh¹,

Klimenko²

2020

YuSU Bull

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New crown-containing imines of 1-hydroxyanthraquinone with chlorine and fluorine atoms in the anthraquinone nucleus were synthesized. For the first time, the thermal and photochemical stages of synthesis are carried out in the solid state (without a solvent). The features of complexation of new chemosensors with cations of alkaline and alkaline earth metals were studied by spectrophotometry. It is shown that the introduction of halogen atoms in the anthraquinone nucleus leads to a significant spectral response. The obtained compounds are tested as components of test systems for visual determining the presence of alkaline earth metal cations in aqueous media.

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Electrochemical transformations and anti/prooxidant activity of sterically hindered o-benzoquinones

Cited by 18 publications

References 60 publications

Catechol‐ and Phenol‐Containing Thio‐Schiff Bases: Synthesis, Electrochemical Properties and Biological Evaluation

Catechol‐ and Phenol‐Containing Thio‐Schiff Bases: Synthesis, Electrochemical Properties and Biological Evaluation

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

Synthesis and properties of halogen-containing macrocyclic anthraquinone imines – chemosensors for metal cations

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