Key result
T-705-ribonucleoside synthesis reveals remarkable heterocycle lability when attached to ribose under mild conditions.
May limit T-705 nucleoside development due to instability; leaves open need for stability studies before further analog pursuit.
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.
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Huchting et al. (2017) studied this question. T-705-ribonucleoside and T-705-ribonucleotide synthesis was evaluated on Synthesis and chemical stability of T-705-ribonucleoside and its 5'-monophosphate. Synthesis of T-705-ribonucleoside and its 5'-monophosphate revealed remarkable lability of the heterocycle when attached to ribose under mild conditions.
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