Abstract
Several series of substituted dehydropiperidine and piperidine-4-carboxylic acid analogs have been designed and synthesized as novel, potent dual PPARalpha/gamma agonists. The SAR of these series of analogs is discussed. A rare double bond migration occurred during the basic hydrolysis of the alpha,beta-unsaturated dehydropiperidine esters 12, and the structures of the migration products were confirmed through a series of 2D NMR experiments.
MeSH terms
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Binding, Competitive / drug effects
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Carboxylic Acids* / chemical synthesis
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Carboxylic Acids* / chemistry
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Carboxylic Acids* / pharmacology
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Dose-Response Relationship, Drug
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Drug Design
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Humans
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Inhibitory Concentration 50
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Molecular Structure
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PPAR alpha / agonists*
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PPAR gamma / agonists*
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Piperidines* / chemical synthesis
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Piperidines* / chemistry
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Piperidines* / pharmacology
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Stereoisomerism
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Structure-Activity Relationship
Substances
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Carboxylic Acids
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PPAR alpha
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PPAR gamma
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Piperidines