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New Syntheses of rac-Huperzine A and its rac-7-Ethyl-Derivative. Evaluation of Several Huperzine A Analogues as Acetylcholinesterase Inhibitors

By Pelayo Camps, Joan Contreras, Rachid El Achab, Jordi Morral-Cardoner, Diego Muñoz-Torrero, Mercè Font-Bardia, Xavier Solans, Albert Badia and Nuria María Vivas

Abstract

rac-Huperzine A, its rac-7-ethyl-derivative and two regioisomeric analogues have been prepared through synthetic sequences involving the elaboration of the pyridone ring in a late stage, by reaction of an intermediate pyrrolidine enamine with propiolamide, which gave mixtures of regioisomeric pyridone derivatives. The acetylcholinesterase inhibitory activity of these and two other recently described 11-unsubstituted huperzine A analogues was determined, the rac-7-ethyl analogue of huperzine A being the most active compound, although it is about 12-fold less active than (−)-huperzine A

Topics: Q1, QD
Publisher: Elsevier
Year: 2000
DOI identifier: 10.1016/s0040-4020(00)00363-x
OAI identifier: oai:eprints.hud.ac.uk:10816
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