Electrochemical behavior and anti/prooxidant activity of thioethers with redox-active catechol moiety

Smolyaninov, I. V.; Pitikova, O. V.; Корчагина, Е. О.; Poddel’sky, Andrey I.; Лужнова, С. А.; Берберова, Н. Т.

doi:10.1007/s00706-018-2264-1

Cited by 15 publications

(18 citation statements)

References 59 publications

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“…Previously, we have reported that catechol thioethers possess antiradical and antioxidant activity. [2,19] In the present work, we continued the study of the antioxidant properties of the synthesized thioethers 1, 3, 5, 7, and 11 by CUPRAC-test, oxidative damage to DNA, and promoted oxidation of glutathione.…”

Section: Antioxidant Activity Of Catechol Thioethersmentioning

confidence: 87%

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New One‐Pot Synthesis of Catechol Thioethers Based on H₂S and Unsaturated Hydrocarbons

et al. 2020

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New one‐pot synthesis of catechol thioethers based on the reaction between H2S, 3,5‐di‐tert‐butyl‐o‐benzoquinone and unsaturated hydrocarbons was developed. This synthetic approach allows to produce target compounds in the media of alkenes or alkynes via an activation of H2S by 3,5‐di‐tert‐butyl‐o‐benzoquinone at room temperature. The method consists in sequential thiolation of an unsaturated hydrocarbon and a sterically hindered o‐benzoquinone. The reaction makes it possible to use hydrogen sulfide as a source of the sulfur atom in the synthesis of biologically active organosulfur compounds. Antioxidant activity of synthesized thioethers in CUPRAC‐test, induced oxidation of DNA or glutathione was determined. The proposed synthetic way is more effective than the synthesis of catechol thioethers via Michael addition of thiols because the formation of disulfide by‐products is reduced. In this study the application of available and cheap reagents such as hydrogen sulfide, alkenes, or alkynes to prepare sterically hindered catechols with thioether group was established.

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Section: Antioxidant Activity Of Catechol Thioethersmentioning

confidence: 87%

“…[a] Data was previously published. [19] Table 3. The change of GSH concentration [μmol L À 1 ] in time in the presence of AAPH and researched catechol thioethers or Trolox.…”

Section: Antioxidant Activity Of Catechol Thioethersmentioning

confidence: 99%

New One‐Pot Synthesis of Catechol Thioethers Based on H₂S and Unsaturated Hydrocarbons

et al. 2020

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“…Additionaly, the second characteristic band of lower intensity in the form of a shoulder to the main band appears in the region of 590 nm, which corresponds to the n-π * transition in quinones. Earlier spectroelectrochemical investigations of catechol L3 have shown that electrolysis at the controlled potential leads to the formation of the corresponding o-benzoquinone [48]. The formation of the o-quinone structure is accompanied by the appearance of a wide absorption band at 400-500 nm.…”

Section: Electrochemistrymentioning

confidence: 98%

“…This fact is also explained by the initial formation of the o-semiquinone radical anion further coordinated to metal. The hyperfine structure of the EPR spectrum of a system "L 3 +PbO 2 " is caused by hyperfine splitting of a signal on the one proton nucleus in the fifth position of the o-semiquinone six-membered carbon ring with a satellite splitting on the magnetic lead isotope ( 207 Pb, 22.1%, I = 1/2): a i ( 1 H) = 2.65 G, a i ( 207 Pb) = 22.75 G [48].…”

Section: Epr Experimentsmentioning

confidence: 99%

“…A similar reaction with dithiols makes it possible to synthesize catechols with a free thio group or bis-catechol thioethers [43,44], which have chelating properties and the ability to be absorbed on the surface [45][46][47]. Variation of the organic groups in thiols allows one to obtain a wide range of thiolated catechols, which exhibit antioxidant, antiradical, and cryoprotective activity [48][49][50]. Transition metal compounds based on sulfur-containing catecholate/o-semiquinolate ligands demonstrate antifungal and antibacterial activity [51,52].…”

Section: Introductionmentioning

confidence: 99%

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Polyfunctional Sterically Hindered Catechols with Additional Phenolic Group and Their Triphenylantimony(V) Catecholates: Synthesis, Structure, and Redox Properties

et al. 2020

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New polyfunctional sterically hindered 3,5-di-tert-butylcatechols with an additional phenolic group in the sixth position connected by a bridging sulfur atom—(6-(CH2-S-tBu2Phenol)-3,5-DBCat)H2 (L1), (6-(S-tBu2Phenol)-3,5-DBCat)H2 (L2), and (6-(S-Phenol)-3,5-DBCat)H2 (L3) (3,5-DBCat is dianion 3,5-di-tert-butylcatecolate)—were synthesized and characterized in detail. The exchange reaction between catechols L1 and L3 with triphenylantimony(V) dibromide in the presence of triethylamine leads to the corresponding triphenylantimony(V) catecholates (6-(CH2-S-tBu2Phenol)-3,5-DBCat)SbPh3 (1) and (6-(S-Phenol)-3,5-DBCat)SbPh3 (2). The electrochemical properties of catechols L1–L3 and catecholates 1 and 2 were investigated using cyclic voltammetry. The electrochemical oxidation of L1–L3 at the first stage proceeds with the formation of the corresponding o-benzoquinones. The second process is the oxidation of the phenolic moiety. Complexes 1 and 2 significantly expand their redox capabilities, owing to the fact that they can act as the electron donors due to the catecholate metallocycle capable of sequential oxidations, and as donors of the hydrogen atoms, thus forming a stable phenoxyl radical. The molecular structures of the free ligand L1 and complex 1 in the crystal state were determined by single-crystal X-ray analysis.

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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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Electrochemical behavior and anti/prooxidant activity of thioethers with redox-active catechol moiety

Cited by 15 publications

References 59 publications

New One‐Pot Synthesis of Catechol Thioethers Based on H₂S and Unsaturated Hydrocarbons

New One‐Pot Synthesis of Catechol Thioethers Based on H₂S and Unsaturated Hydrocarbons

Polyfunctional Sterically Hindered Catechols with Additional Phenolic Group and Their Triphenylantimony(V) Catecholates: Synthesis, Structure, and Redox Properties

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

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Electrochemical behavior and anti/prooxidant activity of thioethers with redox-active catechol moiety

Cited by 15 publications

References 59 publications

New One‐Pot Synthesis of Catechol Thioethers Based on H2S and Unsaturated Hydrocarbons

New One‐Pot Synthesis of Catechol Thioethers Based on H2S and Unsaturated Hydrocarbons

Polyfunctional Sterically Hindered Catechols with Additional Phenolic Group and Their Triphenylantimony(V) Catecholates: Synthesis, Structure, and Redox Properties

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

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New One‐Pot Synthesis of Catechol Thioethers Based on H₂S and Unsaturated Hydrocarbons

New One‐Pot Synthesis of Catechol Thioethers Based on H₂S and Unsaturated Hydrocarbons