Abstract
Based on a pharmacophore hypothesis substituted tetramic and tetronic acid 3-carboxamides as well as dihydropyridin-2-one-3-carboxamides were investigated as inhibitors of undecaprenyl pyrophosphate synthase (UPPS) for use as novel antimicrobial agents. Synthesis and structure-activity relationship patterns for this class of compounds are discussed. Selectivity data and antibacterial activities for selected compounds are provided.
MeSH terms
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Alkyl and Aryl Transferases / antagonists & inhibitors*
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Alkyl and Aryl Transferases / metabolism
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Amides / chemical synthesis
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Amides / pharmacology*
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Cyclization
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Drug Design*
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Enzyme Inhibitors / chemical synthesis
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / pharmacology*
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Escherichia coli / enzymology
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Furans / chemical synthesis
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Furans / pharmacology*
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Microbial Sensitivity Tests
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Molecular Structure
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Polyisoprenyl Phosphates / metabolism
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Protein Conformation
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Pyrrolidinones / chemical synthesis
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Pyrrolidinones / chemistry
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Pyrrolidinones / pharmacology*
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Sesquiterpenes / metabolism
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Streptococcus pneumoniae / drug effects*
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Streptococcus pneumoniae / growth & development
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Structure-Activity Relationship
Substances
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Amides
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Enzyme Inhibitors
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Furans
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Polyisoprenyl Phosphates
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Pyrrolidinones
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Sesquiterpenes
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tetramic acid
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farnesyl pyrophosphate
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Alkyl and Aryl Transferases
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undecaprenyl pyrophosphate synthetase
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tetronic acid