Electrochemical synthesis of selenyl-dihydrofurans via anodic selenofunctionalization of allyl-naphthol/phenol derivatives and their anti-Alzheimer activity

Org Biomol Chem. 2020 Jul 8;18(26):4916-4921. doi: 10.1039/d0ob00629g.

Abstract

Herein, we report an eco-friendly, electrosynthetic approach for the intramolecular oxyselenylation of allyl-naphthol/phenol derivatives. This reaction proceeds with 0.2 equiv. of nBu4NClO4 as an electrolyte and Pt working electrodes in an undivided cell, resulting in the selenyl-dihydrofurans in good to excellent yields. Furthermore, several of the synthesized products presented a high percentage of acetylcholinesterase (AChE) inhibition, highlighting their potential anti-Alzheimer activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholinesterase / metabolism
  • Cholinesterase Inhibitors / chemical synthesis
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / pharmacology*
  • Dose-Response Relationship, Drug
  • Electrochemical Techniques*
  • Electrodes
  • Furans / chemical synthesis
  • Furans / chemistry
  • Furans / pharmacology*
  • Humans
  • Molecular Structure
  • Naphthols / chemistry
  • Naphthols / pharmacology*
  • Organoselenium Compounds / chemical synthesis
  • Organoselenium Compounds / chemistry
  • Organoselenium Compounds / pharmacology*
  • Phenols / chemistry
  • Phenols / pharmacology*

Substances

  • Cholinesterase Inhibitors
  • Furans
  • Naphthols
  • Organoselenium Compounds
  • Phenols
  • Acetylcholinesterase