Molecular docking, derivatization, characterization and biological assays of amantadine

Future Med Chem. 2024;16(18):1853-1863. doi: 10.1080/17568919.2024.2385294. Epub 2024 Aug 9.

Abstract

Background: Derivatization has been tremendously utilized in the field of drug discovery for optimizing the pharmacological properties and improving safety, efficacy and selectivity.Methodology: Schiff's bases (AD1-AD11) are synthesized through amantadine condensation with different aldehydes and ketones. Fourier transform infrared, 1H NMR, 13C NMR, TLC, liquid chromatography mass spectrometry analysis, in silico studies, molecular docking and antiviral activity through hemagglutinin test were performed for evaluation of new compounds.Results: AD2, 3 and 9-11 showed greater antiviral activity than the parent drug. Among all derivatives, AD2 and AD3 exhibited good potential against α-amylase while AD7 and AD10 showed stronger inhibition against α-glucosidase.Conclusion: So, it is concluded that the most potent derivatives can be used as lead compounds in novel drug design of antiviral antidiabetic agents.

Keywords: Schiff’s bases; antiviral; α-amylase; α-glucosidase.

Plain language summary

[Box: see text].

MeSH terms

  • Amantadine* / chemistry
  • Amantadine* / pharmacology
  • Antiviral Agents* / chemistry
  • Antiviral Agents* / pharmacology
  • Glycoside Hydrolase Inhibitors / chemical synthesis
  • Glycoside Hydrolase Inhibitors / chemistry
  • Glycoside Hydrolase Inhibitors / pharmacology
  • Humans
  • Molecular Docking Simulation*
  • Molecular Structure
  • Structure-Activity Relationship
  • alpha-Amylases / antagonists & inhibitors
  • alpha-Amylases / metabolism
  • alpha-Glucosidases / metabolism

Substances

  • Amantadine
  • Antiviral Agents
  • alpha-Amylases
  • alpha-Glucosidases
  • Glycoside Hydrolase Inhibitors