Synthesis, spectral characterization and biological evaluation of phosphorylated derivatives of galanthamine

Eur J Med Chem. 2010 Jan;45(1):203-9. doi: 10.1016/j.ejmech.2009.09.045. Epub 2009 Oct 6.

Abstract

A series of novel phosphorylated derivatives of galanthamine 6-11 and 12-17 were synthesized in two step process with high yields. In the first step galanthamine 1 was reacted with bis (2-chloroethyl) phosphoramidic dichloride 2/4-nitrophenyl phosphorodichloridate 3 in presence of triethylamine (TEA) in dry tetrahydrofuran (THF) yielded the intermediates 4/5. They were further reacted with various compounds like 2-aminoethanol, ethyleneglycol, ethylenediamine, 2-aminoethanethiol, 2-hydroxyethanethiol, monopotassium dihydrogenphosphate to obtain the title compounds 6-11 and 12-17. The title compounds showed promising antimicrobial, antioxidant activities and was greatly influenced by the presence of different bioactive groups.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Antioxidants / chemical synthesis*
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Bacteria / drug effects
  • Catalase / metabolism
  • Galantamine / analogs & derivatives
  • Galantamine / chemical synthesis*
  • Galantamine / chemistry
  • Galantamine / pharmacology*
  • Glutathione / metabolism
  • Lipid Peroxidation / drug effects
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Phosphorylation
  • Rats
  • Rats, Wistar
  • Superoxide Dismutase / metabolism

Substances

  • Anti-Bacterial Agents
  • Antioxidants
  • Galantamine
  • Catalase
  • Superoxide Dismutase
  • Glutathione