Abstract
Abstract 5-Acetoxy- and 5-hydroxyalkanethioamide analogues showed high antibacterial activity against Staphylococcus aureus. Antibacterial thioamides were prepared from 5-alkyl-δ-lactones by amidation, thionation, and subsequent deacetylation. Optically active thioamides with 99% diastereomeric excesses were prepared by diastereomeric resolution using Cbz-L-proline as the resolving agent. Antibacterial thioamides were slowly lactonized by a lipase catalyst. Therefore, these thioamides are potential sustained-release perfume compounds having antibacterial properties.
Highlights
In the past few decades, there has been growing concern about the health hazards and infections caused by pathogenic microorganisms [1]
Antibacterial thioamides were slowly lactonized by a lipase catalyst
When the reaction was performed at -15 °C, rac-4 was obtained in approximately 70% yield, regardless of the difference in the R1 group
Summary
Yasutaka Shimotori*, Masayuki Hoshi, Narihito Ogawa, Tetsuo Miyakoshi and Taisei Kanamoto. Abstract: 5-Acetoxy- and 5-hydroxyalkanethioamide analogues showed high antibacterial activity against Staphylococcus aureus. Antibacterial thioamides were prepared from 5-alkyl-δ-lactones by amidation, thionation, and subsequent deacetylation. Active thioamides with 99% diastereomeric excesses were prepared by diastereomeric resolution using Cbz-L-proline as the resolving agent. Antibacterial thioamides were slowly lactonized by a lipase catalyst. These thioamides are potential sustained-release perfume compounds having antibacterial properties
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