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Sonication‐Assisted Synthesis of (E) ‐2‐Methyl‐but‐2‐enyl Nucleoside Phosphonate Prodrugs
Author(s) -
Bessières Maxime,
Sari Ozkan,
Roy Vincent,
Warszycki Dawid,
Bojarski Andrzej J.,
Nolan Steven P.,
Snoeck Robert,
Andrei Graciela,
Schinazi Raymond F.,
Agrofoglio Luigi A.
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201600879
Subject(s) - prodrug , phosphonate , sonication , chemistry , nucleoside , combinatorial chemistry , stereochemistry , olefin metathesis , olefin fiber , metathesis , organic chemistry , biochemistry , catalysis , chromatography , polymerization , polymer
Several hitherto unknown acyclic 2‐methyl‐but‐2‐enyl nucleoside phosphonate analogs (ANPs) and their bis ‐(pivaloyloxymethyl) prodrug forms were prepared by a challenging ultrasonic‐assisted olefin cross metathesis and further modifications under microwaves, giving rise to a small library of title compounds. These ANPs were evaluated against a wide spectrum of DNA/RNA viruses. Among them, the most active compound exhibited a micromolar anti‐HIV‐1 activity with an EC 50 of 1.1 µM and an EC 90 of 4.2 µM.