New syntheses of rac-Huperzine A and its rac-7-ethyl-derivative. Evaluation of several Huperzine A analogues as acetylcholinesterase inhibitors

Pelayo Camps, Joan Contreras, Rachid El Achab, Jordi Morral, Diego Muñoz-Torrero, Mercè Font-Bardia, Xavier Solans, Albert Badia, Nuria M. Vivas

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15 Citations (Scopus)

Abstract

rac-Huperzine A, its rac-7-ethyl-derivative and two regioisomeric analogue have been prepared though synthetic sequences involving the elaboration of the pyridisne ring in a late stage, by reaction of an intermidiate 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. (C) 2000 Elsevier Science Ltd.
Original languageEnglish
Pages (from-to)4541-4553
JournalTetrahedron
Volume56
Issue number26
DOIs
Publication statusPublished - 23 Jun 2000

Keywords

  • Acetylcholinesterase inhibitory activity
  • Biologically active compounds
  • Polycyclic heterocyclic compounds
  • Pyridones

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