Abstract
The title congeners were synthesized by employing our efficient synthetic route previously explored for preparing enantiomeric pairs of thiolactomycin and its 3-demethyl derivative. While all the synthesized congeners lacked in vitro antibacterial activity, some of the congeners bearing an (E)-cyclohept-2-enylidenemethyl or an (E)-cyclooct-2-enylidenemethyl group were found to exhibit more potent type I FAS inhibitory activity than (S)-3-demethylthiolactomycin having an unnatural configuration.
MeSH terms
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Animals
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Anti-Bacterial Agents / chemistry
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Anti-Infective Agents / chemistry
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Cell Line
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Chemistry, Pharmaceutical / methods*
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Drug Design
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Fatty Acid Synthases / antagonists & inhibitors*
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Fatty Acid Synthases / chemistry
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Humans
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Inhibitory Concentration 50
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Microbial Sensitivity Tests
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Models, Chemical
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Molecular Conformation
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Structure-Activity Relationship
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Thiophenes / chemical synthesis*
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Thiophenes / chemistry
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Thiophenes / pharmacology
Substances
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Anti-Bacterial Agents
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Anti-Infective Agents
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Thiophenes
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thiolactomycin
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Fatty Acid Synthases