Synthesis, Reactions, and Antioxidant Properties of Bis(3-amino-1-hydroxybenzyl)diselenide

Abstract

Bis(3-amino-1-hydroxybenzyl)diselenide containing two ortho groups was synthesized from 7-nitro-3H-2,1-benzoxaselenole and in situ generated sodium benzene tellurolate (PhTeNa). One-pot synthesis of 1,3-benzoselenazoles was achieved from bis(3-amino-1-hydroxybenzyl)diselenide and aryl aldehydes using acetic acid as a catalyst. The X-ray crystal structure of chloro-substituted benzoselenazole revealed a planar structure with T-shaped geometry around the Se atom. Both natural bond orbital and atoms in molecules calculations confirmed the presence of secondary Se···H interactions in bis(3-amino-1-hydroxybenzyl)diselenide and Se···O interactions in benzoselenazoles, respectively. The glutathione peroxidase (GPx)-like antioxidant activities of all compounds were evaluated using a thiophenol assay. Bis(3-amino-1-hydroxybenzyl)diselenide and benzoselenazoles showed better GPx-like activity compared to that of the diphenyl diselenide and ebselen, used as references, respectively. Based on 77Se{1H} NMR spectroscopy, a catalytic cycle for bis(3-amino-1-hydroxybenzyl)diselenide using thiophenol and hydrogen peroxide was proposed involving selenol, selenosulfide, and selenenic acid as intermediates. The potency of all GPx mimics was confirmed by their in vitro antibacterial properties against the biofilm formation of Bacillus subtilis and Pseudomonas aeruginosa. Additionally, molecular docking studies were used to evaluate the in silico interactions between the active sites of the TsaA and LasR-based proteins found in Bacillus subtilis and Pseudomonas aeruginosa.

Aminic Organoselenium Compounds as Glutathione Peroxidase Mimics and Inhibitors of Ferroptosis

“…[42] Short time ago, our ongoing research on aminic organoselenium antioxidants has been focused towards the development of excellent GPx mimics ebselenamine 9 and diselenide 10, consisting of amino group ortho to the Se atom. [43,44] Recently, a new class of organoselenium compound such as benzaselenozoles have been developed as efficient GPx-mimics by our group. [44,45] Herein, continuation of our long-standing interests in the chemistry of organoselenium compounds, we describe the synthesis and antioxidant properties of diarylamine-based organoselenium compounds.…”

“…[43,44] Recently, a new class of organoselenium compound such as benzaselenozoles have been developed as efficient GPx-mimics by our group. [44,45] Herein, continuation of our long-standing interests in the chemistry of organoselenium compounds, we describe the synthesis and antioxidant properties of diarylamine-based organoselenium compounds. In the present work, a new class of aminic organoselenium compounds has been studied for their GPx-like antioxidant properties.…”

“…Recently, the synthesis of Se containing quinoline derivative 8 and its excellent radical scavenging antioxidant activity has been described [42] . Short time ago, our ongoing research on aminic organoselenium antioxidants has been focused towards the development of excellent GPx mimics ebselenamine 9 and diselenide 10 , consisting of amino group ortho to the Se atom [43,44] . Recently, a new class of organoselenium compound such as benzaselenozoles have been developed as efficient GPx‐mimics by our group [44,45] …”

Urea Hydrogen Peroxide and Ethyl Lactate, an Eco-Friendly Combo System in the Direct C(sp2)–H Bond Selenylation of Imidazo[2,1-b]thiazole and Related Structures

“…Similarly, the construction of a C–Se bond is a very important transformation in organic synthesis, as structures with this linkage exhibit fascinating biological and medicinal properties. , Such compounds are renowned for their biological properties, mainly due to their anti-Alzheimer’s, anti-inflammatory, antioxidant, and anticancer activities. − Besides, their role in modern organic chemistry and material science is undeniably very important …”

Glutathione Peroxidase-like Antioxidant Activity of 1,3-Benzoselenazoles: Synthesis and In Silico Molecular Docking Studies as Pancreatic Lipase Inhibitors

“…Having great pharmaceutical and other applications, substituted benzoselenazoles are found to be significant frameworks of Se containing heterocycles . Moreover, benzoselenazole 9 was found to exhibit good GPx-like properties . Also, these benzoselenazoles showed in vitro capabilities against biofilm development by Bacillus subtilis and Pseudomonas aeruginosa.…”