Preparation of secolycorines against acetylcholinesterase

Bioorg Med Chem. 2007 Jan 15;15(2):1034-43. doi: 10.1016/j.bmc.2006.10.026. Epub 2006 Oct 18.

Abstract

5,6-Secolycorines possessing a 5,6-dihydrophenanthridine skeleton were facilely prepared from lycorine through chemical transformations, mainly including N-alkylation, Hofmann degradation type reaction, reductive cleavage of trichloroethylcarbonyl moiety, and hydrogenation. Several secolycorine derivatives showed potent inhibitory activity against acetylcholinesterase with the IC(50) value at micromolar range and are more potent than galanthamine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholinesterase / metabolism*
  • Alkylation
  • Animals
  • Chemical Phenomena
  • Chemistry, Physical
  • Cholinesterase Inhibitors / chemical synthesis*
  • Cholinesterase Inhibitors / pharmacology*
  • Chromatography, Thin Layer
  • Crinum / chemistry*
  • Dose-Response Relationship, Drug
  • Drug Design
  • Eels
  • Galantamine / pharmacology
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Phenanthridines / chemical synthesis*
  • Phenanthridines / pharmacology*
  • Spectroscopy, Fourier Transform Infrared
  • Stereoisomerism

Substances

  • Cholinesterase Inhibitors
  • Indicators and Reagents
  • Phenanthridines
  • Galantamine
  • Acetylcholinesterase