Efficient Synthesis of Highly Active Phospha‐Isosteres of the Influenza Neuraminidase Inhibitor Oseltamivir | Zendy

Carbain Benoit | Zendy; Collins Patrick J. | Zendy; Callum Lori | Zendy; Martin Stephen R. | Zendy; Hay Alan J. | Zendy; McCauley John | Zendy; Streicher Hansjörg | Zendy

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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.

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