New sterically-hindered 6th-substituted 3,5-di- tert -butylcatechols/ o -quinones with additional functional groups and their triphenylantimony(V) catecholates

Poddel’sky, Andrey I.; Arsenyev, Maxim V.; Astaf'eva, Tatyana V.; Чесноков, С. А.; Fukin, Georgy K.; Abakumov, G. A.

doi:10.1016/j.jorganchem.2017.02.035

Cited by 39 publications

(9 citation statements)

References 80 publications

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“…However, in this case there are no remarkable additional interactions between the neighboring pairs. The close situation was observed in crystals of triphenylantimony(V) 3-alkoxy-4,6-di-tert-butylcatecholates and 4,5-dialkoxy-3,6-di-tert-butylcatecholates [ 68 , 103 , 104 ].…”

Section: Resultsmentioning

confidence: 83%

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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Section: Resultsmentioning

confidence: 83%

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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“…It was previously found that 3,5-di- tert -butyl-6-methoxymethylcatechol acts as an alkylating agent in the reactions with activated arenes [ 62 , 63 ] and also interacts with oxygen-, nitrogen-containing nucleophiles [ 64 , 65 ]. In this work, we study the interaction of the above-mentioned catechol with thiols (RSH) mainly containing various biologically active heterocyclic groups ( Scheme 1 ).…”

Section: Resultsmentioning

confidence: 99%

“…The lengths of the oxygen-carbon bonds O(1)–C(1) and O(2)–C(2) as well as the carbon-carbon of the C(1–6) ring are characteristic of catechols [ 25 , 65 , 66 , 67 , 68 ]: O(1)–C(1), 1.377(2) Å; O(2)–C(2), 1.362(2) Å. The carbon-carbon bonds of the six-membered carbon ring C(1–6) average 1.395 ± 0.015 Å and ones are aromatic.…”

Section: Resultsmentioning

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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“… 38 We have also synthesized and characterized some derivatives of 3,5-di- tert -butylcatechol, o -quinones, and their antimony(V) catecholate complexes. 39 − 41 In the present article, we report the structure and electrochemical properties of a number of new alkyl- and aryl-functionalized catecholaldimines and the corresponding 3-iminomethyl- o -benzoquinones.…”

Section: Introductionmentioning

confidence: 99%

Imine-Based Catechols and o-Benzoquinones: Synthesis, Structure, and Features of Redox Behavior

et al. 2020

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Novel sterically hindered catechols of the type 3-(RN=CH)-4,6-DBCatH 2 with iminoalkyl or iminoaryl groups in the third position of the aromatic ring have been synthesized and characterized in detail. The o -benzoquinones 3-(RN=CH)-4,6-DBBQ have been synthesized by the oxidation of the corresponding catechols. The oxidation of methylimino-substituted catechol with K 3 [Fe(CN) 6 ] in alkaline medium leads to the formation of two products: o -quinone and diene–dione, the product of the water addition to the corresponding o -quinone. Some o -benzoquinones react with water or methanol to yield products of water or methanol addition. A prototropic tautomerism is characteristic of catecholaldimines: a quinomethide form is observed in the case of aliphatic amine derivatives, while aryl-substituted catecholaldimines can exist both in the catechol and quinomethide forms in the crystalline state. The formation of dimeric structures motifs is observed in crystals. The electrochemical oxidation of imino-based catechols proceeds via two one-electron processes; the second wave is quasi-reversible, which is unusual for catechols.

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New sterically-hindered 6th-substituted 3,5-di- tert -butylcatechols/ o -quinones with additional functional groups and their triphenylantimony(V) catecholates

Cited by 39 publications

References 80 publications

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

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

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

Imine-Based Catechols and o-Benzoquinones: Synthesis, Structure, and Features of Redox Behavior

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