Article ID Journal Published Year Pages File Type
1377537 Bioorganic & Medicinal Chemistry Letters 2007 4 Pages PDF
Abstract

A series of 7-fluoro-3-aminosteroids were synthesized and their in vitro antimicrobial activities were evaluated against Gram-positive and Gram-negative bacteria. The nucleophilic fluorination of several 7β-hydroxysteroids by diethylaminosulfur trifluoride in n-pentane, followed by reductive amination of the resulting 7-fluoro-3-ketosteroids with spermidine in the presence of NaBH3CN, afforded 7-fluoro-3-aminosteroids in high yield. Compound 25 showed the highest antimicrobial activity against Staphylococcus aureus, Pseudomonas aeruginosa, Streptococcus pyogenes, and Escherichia coli.

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Physical Sciences and Engineering Chemistry Organic Chemistry
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