Abstract
The synthesis and evaluation of novel azetidine lincosamides 1 are described. Eleven new (3-trans-alkyl)azetidine-2-carboxylic acids were synthesized via alkylation of N-TBS-4-oxo-azetidine-2-carboxylic acid and subsequent elaboration then coupled to 7-chloro-1-methylthio-lincosamine. The resulting lincosamides differ from the drug clindamycin in both the size of the ring and the position/structure of the alkyl side-chain. SAR within the series was explored with attention to alkyl variants in positions 1 and 3 of the azetidine ring.
MeSH terms
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Anti-Bacterial Agents / chemical synthesis*
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / pharmacology*
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Azetidines / chemistry*
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Lincosamides
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Macrolides / chemical synthesis*
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Macrolides / chemistry
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Macrolides / pharmacology*
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Microbial Viability / drug effects
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Molecular Structure
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Protein Biosynthesis / drug effects
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Protein Biosynthesis / genetics
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Structure-Activity Relationship
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Transcription, Genetic / drug effects
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Transcription, Genetic / genetics
Substances
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Anti-Bacterial Agents
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Azetidines
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Lincosamides
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Macrolides
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azetidine