4.5 Article

Organylselanyl -Amino Phosphonates: Synthesis, NMR Spectroscopic Study, and Antioxidant and Antinociceptive Activities

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2018, Issue 5, Pages 627-639

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201701565

Keywords

Selenium; Phosphorus; Niobium; Heterogeneous catalysis; NMR spectroscopy; Antioxidants

Funding

  1. FAPESP [2014/23362-8]
  2. FAPERGS [PRONEM 16/2551-0000240-1]
  3. CNPq

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A simple and environmentally benign protocol for the Kabachnik-Fields reaction of aldehydes, selanylamines, and diorganylphosphites catalysed by niobic acid (Nb(2)O(5)nH(2)O) has been described, leading to the formation of selanyl -amino phosphonates under solvent-free reaction conditions. Se-77 {H-1} and P-31{H-1} 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 -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.

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