Synthesis and in vitro assessment of anticholinesterase and antioxidant properties of triazineamide derivatives

Future Med Chem. 2022 Dec;14(23):1741-1753. doi: 10.4155/fmc-2022-0200. Epub 2022 Dec 20.

Abstract

Aim: Cholinesterase inhibitors and radical scavengers have been recognized as powerful symptomatic anti-Alzheimer's disease agents. Hence, the present study aimed to develop new triazineamides as potent anticholinesterase and antioxidant agents. Methods: Triazineamide (7a-i) derivatives were synthesized using cyanuric chloride via nucleophilic substitution followed by condensation. Ellman assay, 2,2-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) radical scavenging assay and molecular docking studies with Autodock 4.2.3 program were conducted. Results: Triazineamide 7c was assessed as a potent, selective and mixed-type dual inhibitor of acetylcholinesterase, with and IC50 of 5.306 ± 0.002 μM, by binding simultaneously with the catalytic active and peripheral anionic sites of acetylcholinesterase, and it had strong 2,2-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) radical scavenging abilities. Conclusion: These results suggest that triazineamides may be of interest to establish a structural basis for new anti-Alzheimer's disease agents.

Keywords: ABTS radical scavenging activity; Alzheimer's disease; cholinesterase; molecular docking.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholinesterase / metabolism
  • Alzheimer Disease* / drug therapy
  • Antioxidants* / chemistry
  • Antioxidants* / pharmacology
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / pharmacology
  • Humans
  • Molecular Docking Simulation
  • Structure-Activity Relationship
  • Sulfonic Acids / chemistry

Substances

  • Antioxidants
  • Cholinesterase Inhibitors
  • Acetylcholinesterase
  • Sulfonic Acids