Electrochemical transformations and antiradical activity of asymmetrical RS-substituted pyrocatechols

Smolyaninov, I. V.; Pitikova, O. V.; Poddel’sky, Andrey I.; Берберова, Н. Т.

doi:10.1007/s11172-018-2299-9

Cited by 15 publications

(12 citation statements)

References 52 publications

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“…They have similar retention times with standard samples in chromatograms. The NMR‐data for synthesized sulfides match completely with the previously obtained results [2] . The retention times of compounds 1 , 3 , 5 and 7 obtained by the Michael reaction [2] are identical with the retention times of these catechol thioethers synthesized by the proposed method.…”

Section: Resultssupporting

confidence: 84%

“…The NMR‐data for synthesized sulfides match completely with the previously obtained results [2] . The retention times of compounds 1 , 3 , 5 and 7 obtained by the Michael reaction [2] are identical with the retention times of these catechol thioethers synthesized by the proposed method. Probably, the main pathway of the reaction is the addition of thiyl radical to the first position of double bond of alkenes.…”

Section: Resultssupporting

confidence: 84%

“…The obtained results indicate that the proposed one‐pot approach turned out to be more effective (75‐82 %) for production of compounds 1 , 3 , 5 than the previously described reaction of Q with thiols in ethanol (45–66 %) [2] . This is due to the suppression of the processes of homocoupling of sulfur‐centered radicals leading to the formation of disulfides [16] …”

Section: Resultsmentioning

confidence: 81%

“…The development of new approaches to the formation of C‐S and S−S bonds is one of the challenges in organic synthesis [1] . Quinoid organosulfur compounds have an ability to expand their redox possibilities due to change in the oxidation state of thioether and o ‐quinone/catechol groups [2] . Besides, o ‐quinones can be used as chelating ligands in coordination chemistry [3] .…”

Section: Introductionmentioning

confidence: 99%

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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: Resultssupporting

confidence: 84%

Section: Resultssupporting

confidence: 84%

Section: Resultsmentioning

confidence: 81%

Section: Introductionmentioning

confidence: 99%

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

et al. 2020

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“…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%

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 transformations and antiradical activity of asymmetrical RS-substituted pyrocatechols

Cited by 15 publications

References 52 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 transformations and antiradical activity of asymmetrical RS-substituted pyrocatechols

Cited by 15 publications

References 52 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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Product

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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