4-Aminopyridine derivatives with antiamnesic activity

Eur J Med Chem. 2000 Jan;35(1):77-82. doi: 10.1016/s0223-5234(00)00103-3.

Abstract

Acetylcholine (Ach) enhancement, useful in the treatment of Alzheimer's disease (AD), may be obtained by means of ion channel modulators such as 4-aminopyridine (4-AP). 4-AP is also the central ring of tacrine, the first drug approved for the treatment of AD. The synthesis and pharmacological activity of three 4-AP derivatives, prepared with the aim of improving their antiamnesic activity, is here described. In two of these compounds 4-AP is connected to 4-aminobutyric acid (GABA), whereas in the third it is connected to 2-indolinone, i.e., the skeleton of linopirdine, another Ach enhancing agent. The new compounds showed potent antiamnesic activity in comparison with piracetam.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Aminopyridine / analogs & derivatives*
  • 4-Aminopyridine / chemistry
  • Alzheimer Disease / drug therapy
  • Aminopyridines / chemical synthesis
  • Aminopyridines / therapeutic use
  • Aminopyridines / toxicity
  • Amnesia / chemically induced
  • Amnesia / drug therapy*
  • Animals
  • Avoidance Learning
  • Carbon Dioxide
  • Indoles / chemical synthesis
  • Indoles / therapeutic use
  • Indoles / toxicity
  • Male
  • Mice
  • Nootropic Agents / chemical synthesis*
  • Nootropic Agents / therapeutic use
  • Piracetam / therapeutic use

Substances

  • (3-(pyridin-4-ylcarbamoyl)propyl)carbamic acid tert-butyl ester
  • 3-(4-aminopyridin-3-ylmethylene)-1,3-dihydroindol-2-one
  • 4-amino-N-pyridin-4-ylbutyramide
  • Aminopyridines
  • Indoles
  • Nootropic Agents
  • Carbon Dioxide
  • 4-Aminopyridine
  • Piracetam