Organoselenium compounds are well-known for their unique biological properties, including antioxidant, anticancer and anti-inflammatory. They result from the presence of a particular Se-moiety enclosed in a structure that provides physicochemical features necessary for effective drug-target interactions. Looking for a proper drug design that considers the influence of each structural element has to be conducted. In this paper, we have synthesized a series of chiral phenylselenides, possessing an additional N-substituted amide moiety, and evaluated their antioxidant and anticancer potential. The presented derivatives, as a group of enantiomeric and diastereomeric pairs, enabled a thorough investigation of the 3D structure-activity dependence in correlation with the presence of the phenylselanyl group as the potential pharmacophore. The N-indanyl derivatives possessing a cis- and trans-2-hydroxy group were selected as the most promising antioxidants and anticancer agents.
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