Flavylium salts as in vitro precursors of potent ligands to brain GABA-A receptors

The synthesis of a series of derivatized flavylium cations was undertaken and the affinity to the benzodiazepine binding site of the GABA-A receptor evaluated. The observed high affinity for some derivatives (sub-μM range) was explained by an in vitro transformation of the flavylium cations into the corresponding trans-retrochalcones, components which are proposed to be the active species in this series.

Graphical abstractThe synthesis of a series of derivatized flavylium cations was undertaken and the affinity to the benzodiazepine binding site on the GABA-A receptor evaluated. The observed high affinity for some derivatives (sub-μM range) was explained by an in vitro transformation of the flavylium cation into the corresponding trans-retrochalcone, component which is proposed to be the active species in this series.Figure optionsDownload full-size imageDownload as PowerPoint slide