Design and synthesis of phenoxy methyl-oxadiazole compounds against Alzheimer's disease

Arch Pharm (Weinheim). 2024 Aug;357(8):e2400115. doi: 10.1002/ardp.202400115. Epub 2024 Apr 24.

Abstract

This study examines the synthesis and evaluation of 11 newly developed compounds as potential anti-Alzheimer's agents that occur via cholinesterase and β-secretase inhibition. The compounds were tested for their inhibitory activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) using the modified Ellman method. The results showed that several compounds exhibited significant inhibition of AChE, particularly compounds 6d, 7a, and 7e, which demonstrated high inhibitory activity at lower concentrations, with IC50 values of 0.120, 0.039, and 0.063 µM, respectively. However, the compounds showed limited effectiveness against BChE, with only a few compounds exhibiting moderate inhibition. Compound 7e showed an inhibitory effect against BACE-1 close to that of the standard drug. Structural analysis revealed that the compounds with substituted benzothiazole and thiazole moieties exhibited the most promising inhibitory activity. This study provides valuable insights into the potential of these synthesized derivatives as a treatment against Alzheimer's disease. Moreover, the structure, stability, and properties of the active compounds were further investigated using density functional theory calculations. As a final note, the utilization of molecular docking and molecular dynamics simulation studies allowed us to elucidate the action mechanism of the active compounds and gain insights into the structure-activity relationship against AChE and β-secretase proteins. These computational techniques provide valuable information on the binding modes, interactions with target enzymes, dynamic behavior, and conformational changes of the compounds, enabling a comprehensive understanding of their biological activity.

Keywords: 1,3,4‐Oxadiazole; cholinesterase; molecular docking; molecular dynamics stimulation; β‐secretase.

MeSH terms

  • Acetylcholinesterase* / metabolism
  • Alzheimer Disease* / drug therapy
  • Amyloid Precursor Protein Secretases* / antagonists & inhibitors
  • Amyloid Precursor Protein Secretases* / metabolism
  • Aspartic Acid Endopeptidases / antagonists & inhibitors
  • Aspartic Acid Endopeptidases / metabolism
  • Butyrylcholinesterase* / metabolism
  • Cholinesterase Inhibitors* / chemical synthesis
  • Cholinesterase Inhibitors* / chemistry
  • Cholinesterase Inhibitors* / pharmacology
  • Dose-Response Relationship, Drug
  • Drug Design*
  • Humans
  • Molecular Docking Simulation*
  • Molecular Dynamics Simulation
  • Molecular Structure
  • Oxadiazoles* / chemical synthesis
  • Oxadiazoles* / chemistry
  • Oxadiazoles* / pharmacology
  • Structure-Activity Relationship

Substances

  • Cholinesterase Inhibitors
  • Oxadiazoles
  • Butyrylcholinesterase
  • Acetylcholinesterase
  • Amyloid Precursor Protein Secretases
  • BACE1 protein, human
  • Aspartic Acid Endopeptidases

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