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

Abstract

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.

Chemical Profiling and Therapeutic Evaluation of Standardized Hydroalcoholic Extracts of Terminalia chebula Fruits Collected from Different Locations in Manipur against Colorectal Cancer

“…A further study found that cyclin D1 promoter activity is inhibited by 2-cyclopenten-1-one [ 47 ].5-Hydroxymethylfurfural has been reported for its antioxidant and antiproliferative activities in human melanoma A375 cells and has great potential application in cancer chemoprevention. The antifungal, anti-inflammatory, antiviral, and antioxidant activities of catechol have been reported in previous studies [ 48 , 49 , 50 , 51 , 52 ].1-Hexyl-2-nitrocyclohexane, hexadecanamide, and 4H-pyran-4-one have also been reported to havea number of biological activities [ 53 , 54 , 55 ]. Moreover, benzeneacetaldehyde (1.56%), 2,3,4,5-tetrahydropyridazine (1.65%), 2,5-furandione, and 3-methyl(1.18%) were some new active constituents found in TYH.…”

2-Mercaptoethanesulfonic Acid as an Effective Free-Radical Scavenger in Perfluorosulfonic Acid Membrane-Based Polymer Electrolyte Membrane Fuel Cells

“…51,59 Possible mechanism of radical scavenging in Nafion-MESA membranes.-The efficacy of sulfur and its thioether compounds as an attractive candidate for radical scavenging and antioxidant activity have been proved for PEMFCs in our earlier work 34 and for other systems by other researchers. 35,36,60 The sulfonate anion moiety (HSCH 2 CH 2 SO 3 − ) of MESA and its sodium salt has shown antioxidant properties in biological systems. 61,62 At the present, however, it is difficult to clearly explain the mechanism of action of MESA in mitigation of oxidative damage of PFSA membranes in PEMFC conditions.…”

Profiling of secondary metabolite and evaluation of anti-diabetic potency of Crotalaria quinquefolia (L): In-vitro, in-vivo, and in-silico approaches

“…The antioxidant potentiality of C. quinquefolia was evaluated using three complementary in vitro experiments, and the findings showed that the extract exhibited significant antioxidant activity. Antioxidant activities of identified polyphenols of the extract namely catechol, hexadecanoic acid, kaempferol, trans -cinnamic acid, quercetin, myricetin, rutin, and 3, 4-dihydroxybenzoic acid have been reported ( Agraharam et al, 2022 , Smolyaninov et al, 2022 ). Additionally, polyphenols are known to have strong anti-diabetic properties and to aid in the control of blood glucose level.…”