An efficient route towards the synthesis of symmetrical diselenide and seleniumcontaining
quinone pseudopeptides via one-pot Ugi and sequential nucleophilic substitution (SN)
methodology was developed. Compounds were evaluated for their antimicrobial and anticancer
activities and their corresponding antioxidant/pro-oxidant profiles were assesed employing 2,2-diphenyl-1-picrylhydrazyl (DPPH),
bleomycin dependent DNA damage and glutathione peroxidase (GPx)-like activity assays. Selenium based quinones were among the
most potent cytotoxic compounds with a slight preference for MCF-7 compared to HepG2 cells and good free radical scavenging activity.
Furthermore, symmetrical diselenides exhibited the most potent GPx-like activity compared to ebselen. Moreover, compounds 7, 8, 9 and
10 exhibited similar antifungal activity to the antifungal drug clotrimazole with modest activity against the Gram-positive bacterium S.
aureus. These results indicate that some of the synthesized organoselenides are redox modulating agent with promising anti-cancer and
Keywords: Anticancer; diselenides, diversity-oriented synthesis (DOS), glutathione peroxidase mimics, isocyanide-based multicomponent
reactions (IMCR), pseudopeptides, selenium-based quinones, Ugi reaction.
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