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.