Abstract
Synthesis of fluorocyclopropyl building blocks, which constitute the core of various therapeutic agents against the hepatitis C virus, is described. The relevant methyl α-amino-β-fluoro-β-vinylcyclopropanecarboxylate has been used as a key intermediate for the total synthesis of a fluorinated analogue of Simeprevir (TMC 435), a HCV NS3/4A protease inhibitor.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Amino Acids, Cyclic / chemical synthesis
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Amino Acids, Cyclic / chemistry
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Amino Acids, Cyclic / pharmacology*
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Antiviral Agents / chemical synthesis
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Antiviral Agents / chemistry
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Antiviral Agents / pharmacology*
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Cell Line
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Cyclopropanes / chemical synthesis
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Cyclopropanes / chemistry
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Cyclopropanes / pharmacology*
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Dose-Response Relationship, Drug
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Hepacivirus / drug effects*
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Hepacivirus / metabolism
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Humans
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Microbial Sensitivity Tests
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Molecular Structure
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Serine Proteinase Inhibitors / chemical synthesis
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Serine Proteinase Inhibitors / chemistry
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Serine Proteinase Inhibitors / pharmacology*
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Structure-Activity Relationship
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Viral Nonstructural Proteins / antagonists & inhibitors*
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Viral Nonstructural Proteins / metabolism
Substances
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Amino Acids, Cyclic
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Antiviral Agents
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Cyclopropanes
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NS3 protein, hepatitis C virus
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NS4 protein, hepatitis C virus
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Serine Proteinase Inhibitors
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Viral Nonstructural Proteins