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A series of new benzofuryl α -azole ketones was synthesized and reduced by asymmetric transfer hydrogenation (ATH). Novel benzofuryl β -amino alcohols bearing an imidazolyl and triazolyl substituents were obtained with excellent enantioselectivity (96-99%). The absolute configuration ( R ) of the products was confirmed by means of electronic circular dichroism (ECD) spectroscopy supported by theoretical calculations. Selected benzofuryl α -azole ketones were also successfully asymmetrically bioreduced by fungi of Saccharomyces cerevisiae and Aureobasidium pullulans species. Racemic and chiral β -amino alcohols, as well as benzofuryl α -amino and α -bromo ketones were evaluated for their antibacterial and antifungal activities. From among the synthesized β -amino alcohols, the highest antimicrobial activity was found for ( R )-1-(3,5-dimethylbenzofuran-2-yl)-2-(1 H -imidazol-1-yl)ethan-1-ol against S. aureus ATCC 25923 (MIC = 64, MBC = 96 μg mL -1 ) and ( R )-1-(3,5-dimethylbenzofuran-2-yl)-2-(1 H -1,2,4-triazol-1-yl)ethan-1-ol against yeasts of M. furfur DSM 6170 (MIC = MBC = 64 μg mL -1 ). In turn, from among the tested ketones, 1-(benzofuran-2-yl)-2-bromoethanones (1-4) were found to be the most active against M. furfur DSM 6170 (MIC = MBC = 1.5 μg mL -1 ) (MIC-minimal inhibitory concentration, MBC-minimal biocidal concentration).

Synthesis, Absolute Configuration, Antibacterial, and Antifungal Activities of Novel Benzofuryl β-Amino Alcohols