title: Toward the Synthesis of Fluorinated Analogues of HCV NS3/4A Serine Protease Inhibitors Using Methyl α-Amino-β-fluoro-β-vinylcyclopropanecarboxylate as Key Intermediate.
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.
authors.forename: Gaëlle
authors.initials: G
authors.lastname: Milanole
authors.forename: Floris
authors.initials: F
authors.lastname: Andriessen
authors.forename: Gérald
authors.initials: G
authors.lastname: Lemonnier
authors.forename: Muriel
authors.initials: M
authors.lastname: Sebban
authors.forename: Gaël
authors.initials: G
authors.lastname: Coadou
authors.forename: Samuel
authors.initials: S
authors.lastname: Couve-Bonnaire
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Bonfanti
authors.forename: Philippe
authors.initials: P
authors.lastname: Jubault
authors.forename: Xavier
authors.initials: X
authors.lastname: Pannecoucke
mesh_terms: D000598:Amino Acids, Cyclic / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D003521:Cyclopropanes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D016174:Hepacivirus / Q000187:drug effects* / Q000378:metabolism; D006801:Humans; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D015842:Serine Proteinase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D017361:Viral Nonstructural Proteins / Q000037:antagonists & inhibitors* / Q000378:metabolism; D012697:Serine Endopeptidases; D043583:Nucleoside-Triphosphatase; D053487:DEAD-box RNA Helicases; D000085242:Viral Proteases
chemical_list: D000598:Amino Acids, Cyclic; D000998:Antiviral Agents; D003521:Cyclopropanes; D015842:Serine Proteinase Inhibitors; D017361:Viral Nonstructural Proteins; C084422:NS3 protein, hepatitis C virus; D012697:Serine Endopeptidases; D043583:Nucleoside-Triphosphatase; D053487:DEAD-box RNA Helicases; D000085242:Viral Proteases; C093542:NS4 protein, hepatitis C virus