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

Overview

Journal Materials (Basel)

Publisher MDPI

Date 2020 Sep 17

PMID 32937873

Citations 2

Authors

Agnieszka Tafelska-Kaczmarek

Renata Kolodziejska

Marcin Kwit

Bartosz Stasiak

Magdalena Wypij

Patrycja Golinska

Affiliations

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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 () 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 and 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 ()-1-(3,5-dimethylbenzofuran-2-yl)-2-(1-imidazol-1-yl)ethan-1-ol against ATCC 25923 (MIC = 64, MBC = 96 μg mL) and ()-1-(3,5-dimethylbenzofuran-2-yl)-2-(1-1,2,4-triazol-1-yl)ethan-1-ol against yeasts of DSM 6170 (MIC = MBC = 64 μg mL). In turn, from among the tested ketones, 1-(benzofuran-2-yl)-2-bromoethanones (1-4) were found to be the most active against DSM 6170 (MIC = MBC = 1.5 μg mL) (MIC-minimal inhibitory concentration, MBC-minimal biocidal concentration).

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