Studies on the synthesis of 1′-CN-triazolyl-<i>C</i>-ribosides

Bozinovic, Nina; Aguiar, Viviane Marques de; Ferry, Angélique; Gallier, Florian; Lubin‐Germain, Nadège; Uziel, Jacques; Miranda, Leandro Soter de Mariz e

doi:10.1039/d2ob01403c

Cited by 2 publications

(1 citation statement)

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“…Remdesivir has a cyan substitution at C1′, which is important for its antiviral activity against SARS-CoV-2 and Ebola virus. [61][62][63] Such 1′-CN-substitution on 1,2,3-triazolyl-Cribonucleosides was studied independently by Lebreton [64] and Miranda/Lubin-Germain [65] (Scheme 16a,b, respectively). Both groups started the synthesis by reacting a corresponding lithium alkylidene with per-O-benzyl-ribonolactone 63.…”

Section: S C H E M E 11mentioning

confidence: 99%

Developments in the chemistry and biology of 1,2,3‐triazolyl‐C‐nucleosides

Nascimento,

Ferry,

Gallier

et al. 2023

Archiv der Pharmazie

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In the last 50 years, nucleoside analogs have been introduced to drug therapy as antivirals for different types of cancer due to their interference in cellular proliferation. Among the first line of nucleoside treatment drugs, ribavirin (RBV) is a synthetic N‐nucleoside with a 1,2,4‐triazole moiety that acts as a broad‐spectrum antiviral. It is on the World Health Organization (WHO) list of essential medicines. However, this important drug therapy causes several side effects due to its nonspecific mechanism of action. There is thus a need for a continuous study of its scaffold. A particular approach consists of connecting d‐ribose to the nitrogen‐containing base with a C–C bond. It provides more stability against enzymatic action and a better pharmacologic profile. The coronavirus disease (COVID) pandemic has increased the need for more solutions for the treatment of viral infections. Among these solutions, remdesivir, the first C‐nucleoside, has been approved by the Food and Drug Administration (FDA) for clinical use against severe acute respiratory syndrome coronavirus 2 (SARS‐CoV‐2). It drew attention to the study of the C‐nucleoside scaffold. Different C‐nucleoside patterns have been synthesized over the years. They show many important activities against viruses and cancer cell lines. 1,2,3‐Triazolyl‐C‐nucleoside derivatives are a prolific and efficient subclass of RBV analogs close to the already‐known RBV with a C–C bond modification. These compounds are often prepared by alkynylation of the d‐ribose ring followed by azide‐alkyne cycloaddition. They are reported to be active against the Crimean‐Congo hemorrhagic fever virus and several tumoral cell lines, showing promising biological potential. In this review, we explore such approaches to 1,2,3‐triazolyl‐C‐nucleosides and their evolution over the years.

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