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

Article abstract of DOI:10.1016/S0040-4020(99)00847-9

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.