Novel derivatives of 3,5-di-tert-butylpyrocatechol with pharmacophore substituents

Ukhin, L. Yu.; ́mina, L. G. Kuz; Alexeenko, Danil V.; Belousova, L. V.; Морковник, А. С.; Шепеленко, Е. Н.; Podshibyakin, Vitaly А.; Бородкин, Г. С.; Dmitrieva, O. I.

doi:10.1007/s11172-019-2702-1

Cited by 3 publications

(2 citation statements)

References 6 publications

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“…Now the development of a new synthetic approach to obtain catechol/hydroquinone thio-ethers and the investigation of their structure and properties has become topical [ 48 , 49 , 50 , 51 , 52 ]. The Michael addition reaction of thiols to ortho -, para -benzoquinones [ 53 , 54 , 55 , 56 ] or nucleophilic substitution [ 57 , 58 ] are often applied to synthesize thio-ethers. The application of molecular iodine or diacetoxyiodo-benzene in the reactions of sulfonating agents with cyclohexanones or with masked o -benzoquinones leads to thiolated catechols [ 59 , 60 ].…”

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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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Section: Introductionmentioning

confidence: 99%

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

et al. 2022

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“…One of state-of-the-art approaches to drug design is the preparation of hybrid compounds combining diff erent pharmacophoric moieties in one molecule. [1][2][3] Phenolic antioxidants exhibit a wide range of biological activity based primarily on their ability to reduce antioxidant stress. 4 Antioxidant therapy is an eff ective strategy for the treatment of numerous diseases.…”

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confidence: 99%

Synthesis of hybrid compounds by benzylation of acylhydrazones with 3,5-di-tert-butyl-4-hydroxybenzyl acetate

et al. 2021

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N-Benzylation of acylhydrazones of the hydroxybenzaldehyde series with 3,5-di-tert-butyl-4-hydroxybenzyl acetate was performed at room temperature in the absence of acid or base catalysts. Carboxamides do not react with 3,5-di-tert-butyl-4-hydroxybenzyl acetate under similar conditions. N-Benzylation of isoniazid and (diphenylphosphoryl)acetic acid hydrazones was shown to be an effi cient method for the synthesis of new hybrid compounds containing moieties of biologically active acylhydrazones and sterically hindered phenols. N-Benzyl derivatives of isoniazid and (diphenylphosphoryl)acetic acid hydrazones containing a hydroxy group at the ortho position of the aromatic ring are formed as individual E isomers with respect to the C=N double bond.

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Modern Trends in the Synthesis of Disulfides: From Metal-Containing Catalysts to Nonmaterial Reagents (Review)

Burmistrova,

Smolyaninov,

Berberova

2023

Russ J Coord Chem

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Novel derivatives of 3,5-di-tert-butylpyrocatechol with pharmacophore substituents

Cited by 3 publications

References 6 publications

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

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

Synthesis of hybrid compounds by benzylation of acylhydrazones with 3,5-di-tert-butyl-4-hydroxybenzyl acetate

Modern Trends in the Synthesis of Disulfides: From Metal-Containing Catalysts to Nonmaterial Reagents (Review)

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