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

Autor(es):Mostrar menos -

Botteselle, Giancarlo V. ^[1] ; Elias, Welman C. ^[2] ; Bettanin, Luana ^[2] ; Canto, Romulo F. S. ^[3] ; Salin, Drielly N. O. ^[2] ; Barbosa, Flavio A. R. ^[2] ; Saba, Sumbal ^[4] ; Gallardo, Hugo ^[2] ; Ciancaleoni, Gianluca ^[5] ; Domingos, Josiel B. ^[2] ; Rafique, Jamal ^[6] ; Braga, Antonio L. ^{[7, 2]}

Afiliação do(s) autor(es)

^[1] Univ Estadual Ctr Oeste UNICENTRO, Dept Quim, BR-85040167 Guarapuava, PR - Brazil

^[2] Univ Fed Santa Catarina UFSC, Dept Quim, BR-88040970 Florianopolis, SC - Brazil

^[3] Univ Fed Ciencias Saude Porto Alegre UFCSPA, Program Posgrad Ciencias Saude, BR-90050170 Porto Alegre, RS - Brazil

^[4] Univ Fed Goias UFG, Inst Quim IQ, BR-74690900 Goiania, Go - Brazil

^[5] Univ Pisa, Dept Chem & Ind Chem, Via G Moruzzi 13, I-56124 Pisa - Italy

^[6] Univ Fed Mato Grosso Sul UFMS, Inst Quim INQUI, BR-79074460 Campo Grande, MS - Brazil

^[7] Univ Johannesburg, Dept Chem Sci, Fac Sci, ZA-2028 Doornfontein - South Africa

• Tipo de documento: Artigo Científico
• Fonte: Molecules; v. 26, n. 15 AUG 2021.
• Citações Web of Science: 0

Resumo

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. (AU)

• Processo FAPESP: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
• Beneficiário: Arlene Gonçalves Corrêa
• Modalidade de apoio: Auxílio à Pesquisa - Programa Centros de Pesquisa em Engenharia