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Efficient Synthesis of Highly Active Phospha‐Isosteres of the Influenza Neuraminidase Inhibitor Oseltamivir
Author(s) -
Carbain Benoit,
Collins Patrick J.,
Callum Lori,
Martin Stephen R.,
Hay Alan J.,
McCauley John,
Streicher Hansjörg
Publication year - 2009
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.200800379
Subject(s) - oseltamivir , neuraminidase , neuraminidase inhibitor , phosphonate , sialidase , virus , virology , chemistry , orally active , zanamivir , lead compound , stereochemistry , microbiology and biotechnology , biology , in vitro , biochemistry , medicine , covid-19 , infectious disease (medical specialty) , pathology , disease
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.