Domino Cyclization/Trifluoromethylation of 2‐Alknylphenols for the Synthesis of 3‐(Trifluoromethyl)benzofurans and Evaluation of their Antibacterial and Antifungal Activities. Issue 5 (19th December 2018)

• Record Type: Journal Article
• Authors: Li, Mengwan; Ye, Yibin; He, Lisi; Hui, Mamie; Ng, Tzi Bun; Wong, Jack Ho; Tsui, Gavin Chit
• Is Part Of: Asian journal of organic chemistry. Volume 8:Issue 5(2019)
• Page Start: 702
• Page End: 709
• Publication Date: 2018-12-19
• Subjects: benzofurans -- trifluoromethylation -- fluoroform -- medicinal chemistry -- inhibitors; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201800651
• Languages: English
• ISSNs: 2193-5807

Abstract

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 (CF3 H). 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‐NH2 C6 H4 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 with2 g elicited a time‐dependent accumulation of reactive oxygen species (ROS). Abstract : How to get rid of bacteria : A strategy for synthesizing 3‐(trifluoromethyl)benzofurans is described. The reaction products showed antibacterial and antifungal activities.