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Domino Cyclization/Trifluoromethylation of 2‐Alknylphenols for the Synthesis of 3‐(Trifluoromethyl)benzofurans and Evaluation of their Antibacterial and Antifungal Activities

Domino Cyclization/Trifluoromethylation of 2‐Alknylphenols for the Synthesis of... Herein, we describe a one‐step synthesis of pharmaceutically relevant 3‐(trifluoromethyl)benzofurans from readily accessible 2‐alkynylphenols. The method utilizes a domino cyclization/trifluoromethylation strategy with [CuCF3] as a reagent. The CF3 source is the low‐cost industrial byproduct fluoroform (CF3H). The assays for antifungal and antibacterial activities conducted on these fluorinated benzofuran derivatives revealed that all were devoid of hemolytic activity toward rabbit erythrocytes indicating absence of toxicity. One of the compounds, 2 g, containing a 4‐NH2C6H4 moiety at the C‐2 position of the benzofuran core, demonstrated suppressive activity against the fungal pathogens Candida albicans, C. glabrata, and the bacterium methicillin‐resistant Staphylococcus aureus, showing minimal inhibitory concentrations (MICs) of 64 μM, 128 μM, and 128 μM, respectively. Incubation of Candida cells with 2 g elicited a time‐dependent accumulation of reactive oxygen species (ROS). http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

Domino Cyclization/Trifluoromethylation of 2‐Alknylphenols for the Synthesis of 3‐(Trifluoromethyl)benzofurans and Evaluation of their Antibacterial and Antifungal Activities

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References (80)

Publisher
Wiley
Copyright
© 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.201800651
Publisher site
See Article on Publisher Site

Abstract

Herein, we describe a one‐step synthesis of pharmaceutically relevant 3‐(trifluoromethyl)benzofurans from readily accessible 2‐alkynylphenols. The method utilizes a domino cyclization/trifluoromethylation strategy with [CuCF3] as a reagent. The CF3 source is the low‐cost industrial byproduct fluoroform (CF3H). The assays for antifungal and antibacterial activities conducted on these fluorinated benzofuran derivatives revealed that all were devoid of hemolytic activity toward rabbit erythrocytes indicating absence of toxicity. One of the compounds, 2 g, containing a 4‐NH2C6H4 moiety at the C‐2 position of the benzofuran core, demonstrated suppressive activity against the fungal pathogens Candida albicans, C. glabrata, and the bacterium methicillin‐resistant Staphylococcus aureus, showing minimal inhibitory concentrations (MICs) of 64 μM, 128 μM, and 128 μM, respectively. Incubation of Candida cells with 2 g elicited a time‐dependent accumulation of reactive oxygen species (ROS).

Journal

Asian Journal of Organic ChemistryWiley

Published: May 1, 2019

Keywords: ; ; ; ;

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