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

Vanessa Nascimento;Pâmella Silva Cordeiro;Massimiliano Arca;Francesca Marini;Luca Sancineto;Antonio Luiz Braga;Vito Lippolis;Michio Iwaoka;Claudio Santi

Supervision

2020-01-01

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Abstract

DFT calculations performed on amidoaryldiselenides as electrophilic derivatives evidenced the presence of a prevalent Se O 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 Se N 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.