Synthesis of a Small Library of Nature-Inspired Xanthones and Study of Their Antimicrobial Activity
Year: 2020
Type: article
Abstract: A series of thirteen xanthones 3–15 was prepared based on substitutional (appendage) diversity reactions. The series was structurally characterized based on their spectral data and HRMS, and the structures of xanthone derivatives 1, 7, and 8 were determined by single-crystal X-ray diffraction. This series, along with an in-house series of aminated xanthones 16–33, was tested for in-vitro antimicrobial activity against seven bacterial (including two multidrug-resistant) strains and five fungal strains. 1-(Dibromomethyl)-3,4-dimethoxy-9H-xanthen-9-one (7) and 1-(dibromomethyl)-3,4,6-trimethoxy-9H-xanthen-9-one (8) exhibited antibacterial activity against all tested strains. In addition, 3,4-dihydroxy-1-methyl-9H-xanthen-9-one (3) revealed a potent inhibitory effect on the growth of dermatophyte clinical strains (T. rubrum FF5, M. canis FF1 and E. floccosum FF9), with a MIC of 16 µg/mL for all the tested strains. Compounds 3 and 26 showed a potent inhibitory effect on two C. albicans virulence factors: germ tube and biofilm formation.
Source: Molecules
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $2,112
Awards: G1027439501, G1167214205, G1319873162, G1417793918, G1516346500, G1578237752, G1763632427, G1949219515, Centro Interdisciplinar de Investigação Marinha e Ambiental, G2342435891, G2626621481, G274581676, G3039528073, Antimicrobianos do mar: modelos de agentes inovadores para reverter a resistência a múltiplos fármacos, G3653605819, G3724168150, G3840324753, G3891694003, G4048552410, G4724859719, Novo: Flavones, Chalcones and Diarylpentanoids as Antitumor Agents: Discovery, Optimization and Structureactivity Relationship Studies. Inicial: Hit to lead optimization of new proapoptotic agents targeting caspases and p53, G491858407, G5224927334, G5454278309, G562452873, G5677667711, G6252076510, G6514921424, G7235202846, Centro Interdisciplinar de Investigação Marinha e Ambiental, G7965899483, G8050799814, G8230709301
OpenAlex ID: W3028498352