Novel Coumarin-Thiadiazole Hybrids and Their Cu(II) and Zn(II) Complexes as Potential Antimicrobial Agents and Acetylcholinesterase Inhibitors

Int J Mol Sci. 2021 Sep 8;22(18):9709. doi: 10.3390/ijms22189709.

Abstract

A series of coumarin-thiadiazole hybrids and their corresponding Cu(II) and Zn(II) complexes were synthesized and characterized with the use of spectroscopic techniques. The results obtained indicate that all the coumarin-thiadiazole hybrids act as bidentate chelators of Cu(II) and Zn(II) ions. The complexes isolated differ in their ligand:metal ratio depending on the central metal. In most cases, the Zn(II) complexes are characteristic of a 1:1 ligand:metal ratio, while in the Cu(II) complexes the ligand:metal ratio is 2:1. All compounds were tested as potential antibacterial agents against Gram-positive (Staphylococcus aureus, Staphylococcus epidermidis) and Gram-negative (Escherichia coli, Pseudomonas aeruginosa) bacterial strains demonstrating activities notably lower than commercially available antibiotics. The more promising results were obtained from the assessment of antineurodegenerative potency as all compounds showed moderate acetylcholinesterase (AChE) inhibition activity.

Keywords: acetylcholinesterase inhibitors; antibacterial activity; antimicrobial; complexes; coumarin; hybrids; neurodegeneration; thiadiazole.

MeSH terms

  • Acetylcholinesterase / chemistry
  • Anti-Bacterial Agents / chemistry
  • Anti-Infective Agents / chemistry*
  • Cholinesterase Inhibitors / pharmacology*
  • Copper / chemistry*
  • Coumarins / chemistry*
  • Crystallography, X-Ray
  • Escherichia coli / drug effects
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Metals
  • Microbial Sensitivity Tests
  • Neurodegenerative Diseases / drug therapy
  • Pseudomonas aeruginosa / drug effects
  • Schiff Bases / chemistry
  • Spectrometry, Fluorescence
  • Spectrophotometry, Atomic
  • Staphylococcus aureus / drug effects
  • Staphylococcus epidermidis / drug effects
  • Thiadiazoles / chemistry*
  • Thiazoles / chemistry
  • Zinc / chemistry*

Substances

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Cholinesterase Inhibitors
  • Coumarins
  • Ligands
  • Metals
  • Schiff Bases
  • Thiadiazoles
  • Thiazoles
  • Copper
  • coumarin
  • Acetylcholinesterase
  • Zinc