Chemical synthesis of galantamine, an acetylcholinesterase inhibitor for treatment of Alzheimer’s disease

Authors: Marco-Contelles, José; Rodríguez, Carolina; García, Antonio G

Source: Expert Opinion on Therapeutic Patents, Volume 15, Number 5, 1 May 2005 , pp. 575-587(13)

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Abstract:

(-)-Galantamine, an alkaloid isolated from the Caucasian snow-drop (Galanthus woronowii), is a selective, reversible and competitive inhibitor of acetylcholinesterase (AChE), as well as an allosteric modulator of the neural nicotinic receptor for acetylcholine. Galantamine is the most recently approved AChE inhibitor for the symptomatic treatment of Alzheimer’s disease. Because of the limited supplies from natural sources, several total syntheses have been reported to produce this drug. Galantamine has attracted both the interest of organic chemists and pharmacologists in a collaborative effort directed to design, prepare and evaluate more biologically active molecules for the treatment of Alzheimer’s disease. In this review the recent patent literature will be reviewed, showing the most important chemical and/or biochemical advances of the chemistry and biology of galantamine.

Keywords: acetylcholinesterase (AChE) inhibitors; Alzheimer’s disease (AD); asymmetric; biogenetic-type synthesis; cyclisation; epi-galantamine; galantamine; intramolecular Heck reaction; narwedine; neural nicotinic receptor for acetylcholine; para–ortho coupling; phenolic oxidative coupling; PIFA; potassium ferricyanide; total synthesis