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

ABSTRACT: A series of new benzofuryl ?-azole ketones was synthesized and reduced by asymmetric transfer hydrogenation (ATH). Novel benzofuryl ?-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 ?-azole ketones were also successfully asymmetrically bioreduced by fungi of Saccharomyces cerevisiae and Aureobasidium pullulans species. Racemic and chiral ?-amino alcohols, as well as benzofuryl ?-amino and ?-bromo ketones were evaluated for their antibacterial and antifungal activities. From among the synthesized ?-amino alcohols, the highest antimicrobial activity was found for (R)-1-(3,5-dimethylbenzofuran-2-yl)-2-(1H-imidazol-1-yl)ethan-1-ol against S. aureus ATCC 25923 (MIC = 64, MBC = 96 ?g mL-1) and (R)-1-(3,5-dimethylbenzofuran-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-ol against yeasts of M. furfur DSM 6170 (MIC = MBC = 64 ?g 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 ?g mL-1) (MIC-minimal inhibitory concentration, MBC-minimal biocidal concentration).

SUBMITTER: Tafelska-Kaczmarek A 

PROVIDER: S-EPMC7560283 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature