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Organylselanyl α‐Amino Phosphonates: Synthesis, NMR Spectroscopic Study, and Antioxidant and Antinociceptive Activities
Author(s) -
Gabriela Vogt Ane,
Perin Gelson,
Luchese Cristiane,
da Silva Patrícia Cecília,
Antunes Wilhelm Ethel,
Santos Silva Márcio
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701565
Subject(s) - chemistry , diastereomer , antioxidant , in vivo , nuclear magnetic resonance spectroscopy , solvent , ex vivo , in vitro , carbon 13 nmr , oxidative stress , proton nmr , stereochemistry , organic chemistry , biochemistry , microbiology and biotechnology , biology
A simple and environmentally benign protocol for the Kabachnik–Fields reaction of aldehydes, selanylamines, and diorganylphosphites catalysed by niobic acid (Nb 2 O 5 · n H 2 O) has been described, leading to the formation of selanyl α‐amino phosphonates under solvent‐free reaction conditions. 77 Se { 1 H} and 31 P{ 1 H} NMR spectroscopy was used for quantification of diastereomeric ratios, mechanistic investigation, and evaluation of the stability of the products. In addition, in‐vitro experiments were carried out to investigate the antioxidant and anticholinesterase activities of the selanyl α‐amino phosphonates. In‐vivo and ex‐vivo experiments were carried out to investigate the potential antinociceptive effect, as well as the acute toxicity. We found that this class of compounds has the potential to act against oxidative stress and to be used for the treatment of painful clinical conditions.