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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 1  6 - 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-9 H -xanthen-9-one ( 7 ) and 1-(dibromomethyl)-3,4,6-trimethoxy-9 H -xanthen-9-one ( 8 ) exhibited antibacterial activity against all tested strains. In addition, 3,4-dihydroxy-1-methyl-9 H -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.

Synthesis of a Small Library of Nature-Inspired Xanthones and Study of Their Antimicrobial Activity