78094-43-6Relevant academic research and scientific papers
First total synthesis of chromanone A, preparation of related compounds and evaluation of their antifungal activity againstCandida albicans, a biofilm forming agent
Bracca, Andrea B. J.,Cordisco, Estefanía,Cortés, Iván,Kaufman, Teodoro S.,Sortino, Maximiliano A.,Svetaz, Laura A.
, p. 19587 - 19597 (2021/06/16)
A straightforward and convenient approach for the first total syntheses of chromanone A and a related 7-OMe substituted natural product is reported. These unique C-3 substituted 2-hydroxymethyl chromones were recently isolated as fungal metabolites. Chromanone A was synthesized in 25.3% overall yield from the readily available pyrocatechol, whereas the second natural product was prepared in 39.7% global yield. A small library of chromones, including both natural products and some of their synthetic heterocyclic precursors, was evaluated againstCandida albicansATCC 10231, a biofilm forming agent. It was found that 8-methoxy-3-methyl-4-oxo-4H-chromene-2-carbaldehyde, a partially oxidized form of chromanone A, exhibited a minimum inhibitory concentration of 7.8 μg mL?1and significantly inhibited the yeast's virulence factors, including the adherence to buccal epithelial cells and the secretion of phospholipases, as well as the formation of germ tubes and the generation of the hyphal pseudomycelium. In addition, despite the heterocycle exhibiting non-significant inhibition of the formation of theCandidabiofilm, it completely inhibited the growth ofC. albicansin preformed biofilms at 62.5 μg mL?1
SYNTHESIS OF ANSAMYCINS: AN APPROACH TO THE NAPHTHOQUINONE PORTION OF THE RIFAMYCINS AND STREPTOVARICINS
Parker, Kathlyn A.,Petraitis, Joseph J.
, p. 397 - 400 (2007/10/02)
Naphthoquinone 1, a fully functionalized model for intermediates in ansamycin synthesis, was prepared by the intramolecular Claisen condensation of benzofuran 9 followed by oxidation of the novel tricyclic compound 10.
