Selenylated Analogs of Tacrine: Synthesis, In Silico and In Vitro Studies of Toxicology and Antioxidant Properties.

Autor: do Sacramento M; LASOL-CCQFA, Universidade Federal de Pelotas - UFPel, P.O. Box 354, 96010-900, Pelotas, RS, Brazil., Morais RB; LASOL-CCQFA, Universidade Federal de Pelotas - UFPel, P.O. Box 354, 96010-900, Pelotas, RS, Brazil., Silveira Lima A; LASOL-CCQFA, Universidade Federal de Pelotas - UFPel, P.O. Box 354, 96010-900, Pelotas, RS, Brazil., Zugno GP; Neurobiotechnology Research Group - GPN, Technological Development Center, Federal University of Pelotas - UFPel, Pelotas, RS, 96160-000, Brazil., de Oliveira RL; Neurobiotechnology Research Group - GPN, Technological Development Center, Federal University of Pelotas - UFPel, Pelotas, RS, 96160-000, Brazil., da Costa GP; LASOL-CCQFA, Universidade Federal de Pelotas - UFPel, P.O. Box 354, 96010-900, Pelotas, RS, Brazil., Savegnago L; Neurobiotechnology Research Group - GPN, Technological Development Center, Federal University of Pelotas - UFPel, Pelotas, RS, 96160-000, Brazil., Alves D; LASOL-CCQFA, Universidade Federal de Pelotas - UFPel, P.O. Box 354, 96010-900, Pelotas, RS, Brazil.
Jazyk: angličtina
Zdroj: Chemistry, an Asian journal [Chem Asian J] 2024 Oct 01; Vol. 19 (19), pp. e202400637. Date of Electronic Publication: 2024 Sep 03.
DOI: 10.1002/asia.202400637
Abstrakt: We present our results on the synthesis and preliminary in silico and in vitro studies of the toxicology and antioxidant properties of selenylated analogs of Tacrine. Initially, we synthesized 2-aminobenzonitriles containing an organic selenium moiety, resulting in sixteen compounds with various substituents linked to the portion derived from diorganyl diselenide. These compounds were then used as substrates in reactions with cyclic ketones, in the presence of 1.4 equivalents of trifluoroboroetherate as a Lewis acid, to synthesize selenylated analogs of Tacrine with yields ranging from 20 % to 87 %. In silico studies explored computational parameters related to antioxidant activity and hepatotoxicity. In vitro studies elucidated the antioxidant effects of Tacrine and its selenium hybrid (TSe) in neutralizing ABTS radicals, scavenging DPPH radicals, and reducing iron ions. Additionally, the acute oral toxicity of one synthesized compound was evaluated.
(© 2024 Wiley-VCH GmbH.)
Databáze: MEDLINE
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