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Synthesis of T‐705‐Ribonucleoside and T‐705‐Ribonucleotide and Studies of Chemical Stability
Author(s) -
Huchting Johanna,
Winkler Matthias,
Nasser Hiba,
Meier Chris
Publication year - 2017
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.201700116
Subject(s) - ribonucleoside , favipiravir , ribonucleotide , lability , nucleobase , stereochemistry , ribonucleotide reductase , chemistry , ribose , mechanism of action , biology , combinatorial chemistry , rna , biochemistry , nucleotide , in vitro , dna , enzyme , protein subunit , medicine , disease , covid-19 , pathology , infectious disease (medical specialty) , gene
T‐705 (favipiravir) is a fluorinated hydroxypyrazine carboxamide that exhibits antiviral activities against a variety of RNA viruses. Given the lack of potent agents to combat these infections caused by a large number of high‐impact pathogens, significant emphasis has been put on studies of the antiviral properties of T‐705 and its mechanism of action. T‐705 acts as a nucleobase analogue; it is therefore metabolized to the corresponding ribonucleoside triphosphate intracellularly. Herein we report a reliable synthesis of T‐705‐ribonucleoside as well as its 5′‐monophosphate. Moreover, we disclose detailed studies on the remarkable lability of the heterocycle when attached to ribose under very mild conditions, as typically applied in biochemical studies.