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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Author(s):
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]
Total Authors: 9
Affiliation:
[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
Total Affiliations: 5
Document type: Journal article
Source: NEW JOURNAL OF CHEMISTRY; v. 44, n. 22, p. 9444-9451, JUN 14 2020.
Web of Science Citations: 0
Abstract

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)

FAPESP's process: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
Grantee:Arlene Gonçalves Corrêa
Support Opportunities: Research Grants - Research Centers in Engineering Program