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

Author(s)

Vogt, Ane Gabriela ^[1] ; Perin, Gelson ^[2] ; Luchese, Cristiane ^[1] ; da Silva, Patricia Cecilia ^[3] ; Wilhelm, Ethel Antunes ^[1] ; Silva, Marcio Santos ^[3]

Affiliation

^[1] Univ Fed Pelotas UFPel, Programa Posgrad Bioquim & Prospeccao, Lab Pesquisa Farmacol Bioquim LaFarBio, GPN, CCQFA, BR-96010900 Capao Do Leao, RS - Brazil

^[2] Univ Fed Pelotas UFPel, Programa Posgrad Quim, Lab Sintese Organ Limpa LASOL, CCQFA, BR-96010900 Capao Do Leao, RS - Brazil

^[3] Univ Fed Abc, CCNH, BR-09210180 Santo Andre, SP - Brazil

• Document type: Journal article
• Source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY; v. 2018, n. 5, p. 627-639, FEB 7 2018.
• Web of Science Citations: 1

Abstract

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. (AU)

• FAPESP's process: 14/23362-8 - Nuclear magnetic resonance to design and chiral discrimination of biocatalytic process
• Grantee: Márcio Santos da Silva
• Support Opportunities: Regular Research Grants