Fast and easy conversion of ortho amidoaryldiselenides into the corresponding ebselen-like derivatives driven by theoretical investigations

Autor(es)

Nascimento, Vanessa ^[1] ; Cordeiro, Pamella Silva ^[1] ; Arca, Massimiliano ^[2] ; Marini, Francesca ^[3] ; Sancineto, Luca ^[3] ; Braga, Antonio Luiz ^[4] ; Lippolis, Vito ^[2] ; Iwaoka, Michio ^[5] ; Santi, Claudio ^[3]

Afiliação do(s) autor(es)

^[1] Univ Fed Fluminense, Dept Quim Organ, Lab Sintese & Aplicacao Substancias Supramol & Or, Outeiro Sao Joao Batista S-N, BR-24020141 Niteroi, RJ - Brazil

^[2] Univ Cagliari, Dipartimento Sci Chim & Geol, SS 554 Bivio Sestu, I-09042 Monserrato, CA - Italy

^[3] Univ Perugia, Dept Pharmaceut Sci, Grp Catalysis Synth & Organ Green Chem, Via Liceo, I-06123 Perugia - Italy

^[4] Univ Fed Santa Catarina, Labselen, Dept Quim, BR-88040900 Florianopolis, SC - Brazil

^[5] Tokai Univ, Dept Chem, Sch Sci, Hiratsuka, Kanagawa 2591292 - Japan

• Tipo de documento: Artigo Científico
• Fonte: NEW JOURNAL OF CHEMISTRY; v. 44, n. 22, p. 9444-9451, JUN 14 2020.
• Citações Web of Science: 0

Resumo

DFT calculations performed on amidoaryldiselenides as electrophilic derivatives evidenced the presence of a prevalent SeMIDLINE HORIZONTAL ELLIPSISO weak interaction when selenium is bonded to a Se atom (diselenides), a Br atom (selenenyl bromide) and an O atom (selenenic acid), while for selenenyl iodide derivatives, a prevalent contribution of the SeMIDLINE HORIZONTAL ELLIPSISN interaction was predicted. This in silico observation has been experimentally exploited for the efficient synthesis of a small library of N-substituted benzoisoselenazol-3(2H)-ones and benzoisothiazol-3(2H)-ones considering the pharmacological relevance of ebselen recently reported also as an antiviral agent against Sars-Cov2. (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