Antiradical activity of morpholine- and piperazine-functionalized triphenylantimony(V) catecholates

Smolyaninov, I. V.; Poddel’skii, A. I.; Antonova, N. A.; Smolyaninova, S. A.; Берберова, Н. Т.

doi:10.1134/s1070328413020073

Cited by 19 publications

(6 citation statements)

References 36 publications

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“…We have previously shown that triarylantimony (V) complexes with catecholate ligands act as effective traps and can not only intercept molecular oxygen, but also neutralize alkylperoxy radicals and DPPH, promote the destruction of hydroperoxides, and inhibit lipid peroxidation processes [ 75 , 76 , 77 , 78 , 79 , 80 ]. In the continuation of our research, it was interesting to evaluate the effect of the RS group on the radical scavenging activity in the reaction with the stable DPPH radical.…”

Section: Resultsmentioning

confidence: 99%

“…In contrast to the transition metals, the O 2 binding does not lead to a change in the antimony oxidation state, while the redox active ligand is involved in the redox reaction. The nature of functional groups in redox active ligands [ 65 , 66 , 67 , 68 ], as well as in substituents at a central antimony atom [ 69 , 70 , 71 , 72 , 73 , 74 ], affects the redox properties of antimony catecholates and their antioxidant activity [ 75 , 76 , 77 , 78 , 79 , 80 ]. Electron-donating groups in catecholate or at the antimony atom in complexes of the type CatSbR 3 shift the oxidation potential to the anodic region.…”

Section: Introductionmentioning

confidence: 99%

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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: 99%

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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“…Compound 1 combines in its structure a hydrophobic organometallic fragment with a redox‐active ligand capable to exist in several redox forms. Organometallic antimony(V) derivatives with redox‐active ligands have been found to manifest antiradical activity …”

Section: Introductionmentioning

confidence: 99%

The influence of triphenylantimony(V) catecholate and its spiroendoperoxide on lipid peroxidation

Smolyaninov

Antonova

Poddel’sky

et al. 2014

Applied Organom Chemis

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The effects of triphenylantimony(V) catecholate Ph 3 Sb(Cat) (1) and its spiroendoperoxide Ph 3 Sb(L-O 2 ) (2) (Cat = 3,6-di-tert-butyl-4,5-dimethoxycatecholate) on lipid peroxidation (LP) in vitro and in vivo were examined in BALB/c line mice. A comparative study of the impact of compounds 1 and 2 on LP under similar conditions was made by measuring the formation of thiobarbituric acid reactive substances (TBARS). The anti-or pro-oxidant action of complexes 1 and 2 may be caused by the different redox level of the ligand acting as radical scavenger and/or by the bound molecular oxygen promoting the oxidation process. Biological experiments (in vitro and in vivo) were performed using mouse tissue homogenates. Decreasing TBARS concentration was observed in all examined tissues and blood serum (in vitro as well as in vivo) for catecholate 1. These results indicate inhibition of LP in the presence of complex 1. In contrast to 1, spiroendoperoxide 2 increases the level of TBARS in tissue homogenates. Minor fluctuations of TBARS concentration in erythrocytes and in blood serum indicate the absence of an obvious anti/pro-oxidant influence of 2 on the LP process in vivo. The role of catecholate fragment was found to be essential in explaining antioxidant properties.

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“…In [2,8] we showed that triphenylantimony(V) complexes with redox-active ligands exhibit pronounced antiradical activity and revealed a reverse correlation between inhibitory activity and oxidation potential. To provide further evidence for such correlation, in the present work we studied the antiradical activity of complexes I-III and 3,6-di-tertbutyl-4,5-dimethoxy-о-benzoquinone in the autooxidation of oleic acid at 60°С.…”

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confidence: 97%

“…Electron-donating substituent group in the redox-active fragment facilitates O 2 binding, shifts anodic oxidation potentials to the cathodic region, and enhances the antiradical activity of Sb(V) compounds [7,8]. Electron withdrawing groups in the catecholate ligand increase the potentials of the catecholate-о-semiquinolate-о-benzoquinone redox transitions and sometimes alter the mechanism of electrochemical oxidation of triphenylantimony(V) catecholate complexes from a two-stage one-electron transfer to one-stage two-electron transfer process [9,10].…”

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confidence: 99%

Redox transformations and antiradical activity of triarylantimony(V) 3,6-di-tert-butyl-4,5-dimethoxycatecholates

et al. 2014

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Triarylantimony(V) catecholate complexes were synthesized by the oxidative addition of 3,6-ditert-butyl-4,5-dimethoxy-o-benzoquinone to triarylstibines. The electrochemical properties and antiradical activity of the synthesized compounds were studied. According to cyclic viltammetry data, the complexes are oxidized via two consecutive quasi-reversible stages. Introduction of halogen atoms in para-position of phenyl groups at Sb(V) causes anodic shifts of the oxidation potentials and enhances stability of the mono-and dicationic forms of the compounds, which form in the course of electrochemical transformations. Triarylantimony(V) catecholate complexes exhibit appreciable antiradical activity in the auto-oxidation of oleic acid. In was found that the inhibitory activity of the complexes depends on their redox potential.Previously we showed that the redox characteristics, antiradical activity of organo-antimony(V) complexes with redox-active ligands, as well as their ability to bind molecular oxygen depends on a variety of factors [1-6]. Electron-donating substituent group in the redox-active fragment facilitates O 2 binding, shifts anodic oxidation potentials to the cathodic region, and enhances the antiradical activity of Sb(V) compounds [7,8]. Electron withdrawing groups in the catecholate ligand increase the potentials of the catecholate-о-semiquinolate-о-benzoquinone redox transitions and sometimes alter the mechanism of electrochemical oxidation of triphenylantimony(V) catecholate complexes from a two-stage one-electron transfer to one-stage two-electron transfer process [9, 10]. The stability of the cationic complexes resulting from electrochemical oxidation is also affected by the nature of the heteroatoms forming five-membered N, O,Oor S,. The properties of Sb(V) catecholate complexes can also be varied not only by varying substituents in the redox-active ligand, but also by functionalizing groups linked to the central antimony atom [15]. In the present work we continued to study the effect of aryl substituents (phenyl, pchlorophenyl, p-fluorophenyl) in the organometallic fragment SbR 3 of triarylantimony(V) 3,6-di-tert-butyl-4,5-dimethoxycatecholate complexes on the electrochemical transformations and antiradical activity in the auto-oxidation of oleic acid.We have synthesized triphenylantimony, tri-pchlorophenyl-, and tri-p-chlorophenylantimony catecholate complexes I-III by the oxidative addition of the corresponding triarylstibines to 3,6-di-tert-butyl-4,5-dimethoxy-о-benzoquinone (Scheme 1).Complex I was described in [5]. Complexes II and III were characterized by 1 H and 13 C NMR spectroscopy and mass spectrometry; their structure was found to be consistent with the suggested formulas. The oxidation potential relates to the reducing ability of a compound and is a factor which allows one to predict the antiradical activity. The electrochemical

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Antiradical activity of morpholine- and piperazine-functionalized triphenylantimony(V) catecholates

Cited by 19 publications

References 36 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

The influence of triphenylantimony(V) catecholate and its spiroendoperoxide on lipid peroxidation

Redox transformations and antiradical activity of triarylantimony(V) 3,6-di-tert-butyl-4,5-dimethoxycatecholates

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