1-INDANONE DERIVATIVES: A NOVEL ONE-POT APPROACH TO IMIDES VIA BECKMANN-LIKE REARRANGEMENT AND THEORETICAL INSIGHTS INTO THEIR INTERACTIONS WITH AChE ENZYME

The reaction of (E)-2,3-dihydro-1H-inden-1-one oxime (3) with carboxylic acid anhydrides and fatty acids aiming at the formation of the respective esters unexpectedly produced imides [5a-5c and 5d-5k] (81-95% yields). This work proposes the formation of these imides from the oxime (3) through a mechanism using an oxaziridine as an intermediate, followed by a Beckmann-like rearrangement. However, in the presence of nucleophilic catalysts [dimethylaminopyridine (DMAP) and dicyclohexylcarbodiimide (DCC)] instead of electrophilic ones. Products were characterized by spectral analysis [NMR (1H / 13C) and MS (EIMS / HRMS)]. In the in silico study, the competition of some oxime derivatives was remarkable compared to galantamine (GNT) and its bioactive interactions with the main amino acid residues that are part of the site of interest of cholinesterase activity. The calculation of the physicochemical properties through molecular modeling also allowed us to understand the interaction between a ligand and its receptor, indicating the derivatives 5i, 5g, and 5h as promising acetylcholinesterase inhibitors.