N-Substituted Azaaurones: Synthesis and Photochemistry

Abstract

Aurones are a sub-family of natural compounds in the flavonoid family found in plants. Recent research has shown progress in the synthesis of aurones and their therapeutic potential as anti-cancer, anti-fungal, anti-microbial, and anti-inflammatory agents. Observations have found that substituting functional groups and switching between E and Z isomers of aurones can optimize the activity of the compound. This research attempted the synthesis of the azaaurone 2-(4-Methylbenzylidene)-1,2-dihydro-3H-indol-3-one. This parent azaaurone was successfully substituted at the intracyclic nitrogen through N-alkylation and N-acetylation. The possibility of reversibly photoisomerizing between the Z and E isomers of each compound was also studied with the intention of opening new options for photoswitches and to explore the biological application of these isomers. The absorption spectra were identical for each isomer, so it was concluded that this compound was not ideal for reversible isomerization.