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Synthesis and UV studies of a small library of 6-aryl-4-hydroxy-2- pyrones. A relevant structural feature for the inhibitory property of arisugacin against acetylcholinesterase

  • Christopher J. Douglas
  • , Heather M. Sklenicka
  • , Hong C. Shen
  • , David S. Mathias
  • , Shane J. Degen
  • , Geoffrey M. Golding
  • , Christopher D. Morgan
  • , Regina A. Shih
  • , Kristen L. Mueller
  • , Lisa M. Seurer
  • , Erik W. Johnson
  • , Richard P. Hsung

Research output: Contribution to journal › Article › peer-review

Abstract

4-Hydroxypyrones belong to an important class of compounds not only because of their medicinal significance, but also because they represent a common structural feature among natural products that are biologically relevant. We describe here preparations of a small library of 6-aryl-4- hydroxy-pyrones which represent structural analogs of the DE-ring of arisugacin, a potent and selective inhibitor against acetylcholinesterase. Given the structural significance of the DE-ring in the inhibitory activity of arisugacin, chemical shifts of relevant protons on the pyrone ring are compared, and distinct features in UV absorptions of these 6-aryl-4-hydroxy- pyrones are described.

Original languageEnglish (US)
Pages (from-to)13683-13696
Number of pages14
JournalTetrahedron
Volume55
Issue number48
DOIs
StatePublished - Nov 26 1999

Keywords

  • Electronic Effects
  • Electronic Spectra
  • NMR
  • Pyrones

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