Design, Synthesis and Biological Evaluation of Novel Triazole N-acylhydrazone Hybrids for Alzheimer's Disease

Molecules. 2020 Jul 10;25(14):3165. doi: 10.3390/molecules25143165.

Abstract

Alzheimer's disease (AD) is a multifactorial neurodegenerative disorder that involves different pathogenic mechanisms. In this regard, the goal of this study was the design and synthesis of new compounds with multifunctional pharmacological activity by molecular hybridization of structural fragments of curcumin and resveratrol connected by an N-acyl-hydrazone function linked to a 1,4-disubstituted triazole system. Among these hybrid compounds, derivative 3e showed the ability to inhibit acetylcholinesterase activity, the intracellular formation of reactive oxygen species as well as the neurotoxicity elicited by Aβ42 oligomers in neuronal SH-SY5Y cells. In parallel, compound 3e showed a good profile of safety and ADME parameters. Taken together, these results suggest that 3e could be considered a lead compound for the further development of AD therapeutics.

Keywords: Alzheimer’s disease; curcumin; molecular hybridization; resveratrol.

MeSH terms

  • Acetylcholinesterase / metabolism
  • Alzheimer Disease / drug therapy*
  • Alzheimer Disease / metabolism
  • Amyloid beta-Peptides / metabolism
  • Cells, Cultured
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / pharmacokinetics
  • Cholinesterase Inhibitors / pharmacology
  • Curcumin / pharmacokinetics
  • Curcumin / pharmacology
  • Humans
  • Neurons / drug effects
  • Neurons / metabolism
  • Neuroprotective Agents / chemistry
  • Neuroprotective Agents / pharmacokinetics
  • Neuroprotective Agents / pharmacology
  • Pharmacokinetics
  • Reactive Oxygen Species / metabolism
  • Resveratrol / pharmacokinetics
  • Resveratrol / pharmacology
  • Triazoles / chemistry*
  • Triazoles / pharmacokinetics
  • Triazoles / pharmacology*

Substances

  • Amyloid beta-Peptides
  • Cholinesterase Inhibitors
  • Neuroprotective Agents
  • Reactive Oxygen Species
  • Triazoles
  • Acetylcholinesterase
  • Curcumin
  • Resveratrol