Abstract
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-(1H-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-(1H-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).
Highlights
Benzofuran is considered as a very important oxygen-containing heterocyclic compound due to its diverse biological profile [1]
The compounds were obtained by the corresponding amino ketones
In our previously published research, we have proved that the asymmetric transfer hydrogenation
Summary
Benzofuran is considered as a very important oxygen-containing heterocyclic compound due to its diverse biological profile [1]. Many of the clinically approved medicines are synthetic and naturally occurring substituted benzofuran derivatives which display various biological (antitumor, antiarrhythmic, antidepressant, antihyperglycemic, antimicrobial, antibiotic, antiparasitic) activities. The most recognized synthetic drug is amiodarone, a highly effective antiarrhythmic agent with class III activity, used for both, ventricular and supraventricular types of arrhythmia [2]. Saprisartan is used in the treatment of hypertension and heart failure [3] whereas vilazodone is a medication used to treat major depressive disorders [4].
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