title: Efficient synthesis of highly active phospha-isosteres of the influenza neuraminidase inhibitor oseltamivir.
abstract: With a Hunsdiecker-Barton iododecarboxylation strategy, we converted the carboxylate group of the oseltamivir precursor into exemplary phosphonate monoesters. In all cases, K(i) values towards influenza virus sialidase remained in the sub-nanomolar range. We have thus made valuable structural space available for the design of novel oseltamivir-based tools for influenza virus research.
authors.affiliation: Department of Chemistry and Biochemistry, University of Sussex, Brighton, BN1 9QG, UK.
authors.forename: Benoit
authors.initials: B
authors.lastname: Carbain
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Collins
authors.forename: Lori
authors.initials: L
authors.lastname: Callum
authors.forename: Stephen R
authors.initials: SR
authors.lastname: Martin
authors.forename: Alan J
authors.initials: AJ
authors.lastname: Hay
authors.forename: John
authors.initials: J
authors.lastname: McCauley
authors.forename: Hansjörg
authors.initials: H
authors.lastname: Streicher
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D006801:Humans; D009980:Influenza A virus / Q000187:drug effects*; D009439:Neuraminidase / Q000037:antagonists & inhibitors / Q000378:metabolism*; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry; D053139:Oseltamivir / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: D000998:Antiviral Agents; D063065:Organophosphonates; D053139:Oseltamivir; D009439:Neuraminidase