Add time:08/16/2019 Source:sciencedirect.com
The in vitro antifungal activity of a novel series of cis- and trans-5-{[aryl or aryloxy (or thio)]methyl}-3-(1 H-imidazol-1-ylmethyl)-3-(2-thienyl)-2-methylisoxazolidines (13–24) was evaluated and compared with ketoconazole. The title series of compounds was prepared via a 1,3-dipolar cycloaddition reaction of 1-(2-thienyl)-2-(1 H-imidazol-1-yl)-N-methylethanimine N-oxides with appropriate styrenes, allyl phenyl ethers, or allyl phenyl thioether precursors. The resulting products were mixtures of the corresponding cis- and trans-diastereomers which were readily separated by flash chromatography on neutral silica gel. The majority of compounds 13–24, when tested in solid agar cultures, exhibited moderate to potent activity against Trichophyton rubrum, Aspergillus fumigatus, and Candida albicansat concentrations ranging between ≦2.0 and 70.0 μg/mL.
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