Total synthesis of a sorrentanone ester library and evaluation of its antimicrobial potential

Abstract

Abstract Sorrentanone belongs to the class of monomeric sorbicillinoids and displays bioactivities against various Gram-positive bacteria including Bacillus subtilis, Enterococcus faecalis, and Streptococcus as well as Staphylococcus species. Within this work, we present the optimization of the synthetic access towards the sorrentanone scaffold, facilitating the formation of a focused library of structural analogs with ester side chains. Exploration of the bioactivities of this compound library displayed the improvement of antibacterial properties and the presence of additional antifungal activities. Initial mode of action analyses showed the influence of the compounds on fungal filament propagation and biofilm production. Overall, this work reveals the pharmaceutical relevance of less studied monomeric sorbicillinoids.