First total synthesis of chromanone A, preparation of analogues and evaluation of their bioactivity.

CORTÉS, I., ; CORDISCO, E., ; KAUFMAN, T., ; SORTINO, M., ; SVETAZ, L.,; BRACCA, A..

Congreso; LatinXChem2021; 2021

Biofilms are structured microbial communities, embedded in a self-produced polymeric matrix of protein and polysaccharides. These enduring structures are elusive to the defense system of the host, reluctant to undergo phagocytosis, and offer the producing microorganism a markedly increased resistance to antibiotics and chemical disinfectants. Therefore, biofilms are an important form of microbial resistance and transmission of chronic infections. In this context, there is a need for antimicrobial agents capable of attacking microorganisms within the biofilms. Hence, the search for new compounds endowed with this property is currently relevant. The chromone skeleton is a “privileged structure”, meaning a promising motif for drug development. Not surprisingly, substituted chromones are known to display a variety of useful biological properties, including antifungal activity. In 2009, Gamal-Eldeen and coworkers reported the isolation of chromanone A, from an algicolous marine Penicillium species, cultivated on a solid biomalt medium. In turn, this fungus was isolated as an endophyte of the Egyptian green alga Ulva sp. The natural product inhibits the activity of CYP1A at a level of 4 mg/mL, which turns it into a potential cancer chemopreventive agent.1Being a member of the very small family of the naturally occurring 2- hydroxymethylchromones which bear a C-3 functionalization, chromanone A is a structurally unique chromone.