The Beckmann Rearrangement Applied to Ursolic Acid with Antimalarial Activity in Medicinal Chemistry Studies

Abstract

The A ring-expanded derivative of ursolic acid and the corresponding fragmentation product were obtained through the Beckmann rearrangement under optimized reaction conditions. A mechanistic approach was taken in order to explain both the specificity of the rearrangement and the fragmentation of the cycle. The intermediates and the final products of the route were evaluated for antimalarial activity. Keywords: Antimalarial, Beckmann rearrangement, Beckmann fragmentation, triterpene, ursolic acid, thionyl chloride, aromatase, nitrogen, bioactive compounds, nitrile