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Catalytic Antioxidant Activity of Bis-Aniline-Derived Diselenides as GPx Mimics.

ABSTRACT: Herein, we describe a simple and efficient route to access aniline-derived diselenides and evaluate their antioxidant/GPx-mimetic properties. The diselenides were obtained in good yields via ipso-substitution/reduction from the readily available 2-nitroaromatic halides (Cl, Br, I). These diselenides present GPx-mimetic properties, showing better antioxidant activity than the standard GPx-mimetic compounds, ebselen and diphenyl diselenide. DFT analysis demonstrated that the electronic properties of the substituents determine the charge delocalization and the partial charge on selenium, which correlate with the catalytic performances. The amino group concurs in the stabilization of the selenolate intermediate through a hydrogen bond with the selenium.

SUBMITTER: Botteselle GV

PROVIDER: S-EPMC8347129 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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Catalytic Antioxidant Activity of Bis-Aniline-Derived Diselenides as GPx Mimics.

Botteselle Giancarlo V GV Elias Welman C WC Bettanin Luana L Canto Rômulo F S RFS Salin Drielly N O DNO Barbosa Flavio A R FAR Saba Sumbal S Gallardo Hugo H Ciancaleoni Gianluca G Domingos Josiel B JB Rafique Jamal J Braga Antonio L AL

Molecules (Basel, Switzerland) 20210723 15

Herein, we describe a simple and efficient route to access aniline-derived diselenides and evaluate their antioxidant/GPx-mimetic properties. The diselenides were obtained in good yields via ipso-substitution/reduction from the readily available 2-nitroaromatic halides (Cl, Br, I). These diselenides present GPx-mimetic properties, showing better antioxidant activity than the standard GPx-mimetic compounds, ebselen and diphenyl diselenide. DFT analysis demonstrated that the electronic properties ...[more]

PMID: 34361597

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