Synthesis of novel <i>C</i>-nucleoside analogues bearing an anomeric cyano and a 1,2,3-triazole nucleobase as potential antiviral agents

Sierocki, Pierre; Gaillard, Krystal; Arellano-Reyes, Ruben Arturo; Donnart, Chloé; Lambert, Emilie; Grosse, Sandrine; Arzel, Laurence; Tessier, Arnaud; Guillemont, Jérôme; Mathé-Allainmat, Monique; Lebreton, Jacques

doi:10.1039/d1ob02451e

Cited by 10 publications

(6 citation statements)

References 34 publications

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“…During the preparation of the present manuscript, Lebreton and co-workers published a study of a very similar approach to the synthesis of compounds like 30a , 30b and 32 . 16 As also observed herein, the authors reported difficulties with the cyanation reaction of a protected 4,5-disubstituted triazole ring embedded in a perbenzyl riboside. In our case, the synthesis of an intermediate such as 27 solves this problem by delivering the corresponding protected intermediates 30a and 30b in a 43% global yield from lactone 19 .…”

supporting

confidence: 70%

“…Similar observations concerning the difficulty in amidating unprotected C1′ quaternized triazolyl-C-ribonucleosides have been recently observed. 16 In the case of 30a and 30b, a mixture of products could be detected after heating overnight at 50 °C. Separation of these products from the mixture proved to be a very difficult task, and only partial purification of a product with a protonated exact mass of 630.2717 Da was possible.…”

Section: Organic and Biomolecular Chemistry Papermentioning

confidence: 98%

“…Similar observations concerning the difficulty in amidating unprotected C1′ quaternized triazolyl- C -ribonucleosides have been recently observed. 16…”

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confidence: 99%

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Studies on the synthesis of 1′-CN-triazolyl-C-ribosides

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confidence: 70%

Section: Organic and Biomolecular Chemistry Papermentioning

confidence: 98%

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Studies on the synthesis of 1′-CN-triazolyl-C-ribosides

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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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“…1 The nucleoside analogues display great anti-tumor and antiviral activities and have become cornerstones of treatment for cancer and viral infections (Figure 1, Table 1). [2][3][4][5][6][7][8][9][10][11] Numerous bioactive modified nucleosides have been produced as a result of the extended quest for clinically relevant nucleoside derivatives. Recent years have seen a lot of research on the conformational restriction of the ribose or deoxyribose furanose ring in the nucleosides, nucleotides, and oligonucleotides.…”

Section: Introductionmentioning

confidence: 99%

Advances in the Synthesis of Spirocyclic Nucleosides

Kumar,

Khan,

Arora

et al. 2023

Synthesis

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The nucleosides are the building blocks for nucleic acids and composed of a five-carbon sugar bearing either pyrimidine or purine nucleobase. The biological properties of nucleosides can be tailored by chemically modifying the five-carbon sugar to influence its sugar pucker. The spirocyclic scaffold is an indispensable scaffold in more than ten approved drugs, and its inherent three-dimensionality makes it an ideal modification to influence the sugar pucker and biological properties of nucleosides. However, the introduction of spirocyclic scaffold is often synthetically challenging due to increase in synthetic steps and stereocenters. The present review highlights the advances in synthetic methodologies developed during the past decades for accessing various members of the spiro-functionalized nucleoside family.1 Introduction2 C-1′-Spirocyclic Nucleosides3 C-2′-Spirocyclic Nucleosides4 C-3′-Spirocyclic Nucleosides5 C-4′-Spirocyclic Nucleosides6 Miscellaneous Spirocyclic Nucleosides7 Conclusion and Future Perspectives

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Synthesis of novel C-nucleoside analogues bearing an anomeric cyano and a 1,2,3-triazole nucleobase as potential antiviral agents

Abstract: A linear sequence to access to a novel series of C-nucleosides bearing a quaternary carbon at the anomeric position tethered to a 4-substituted 1,2,3-triazole ring is described. Most of the...

Cited by 10 publications

References 34 publications

Studies on the synthesis of 1′-CN-triazolyl-C-ribosides

Studies on the synthesis of 1′-CN-triazolyl-C-ribosides

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

Advances in the Synthesis of Spirocyclic Nucleosides

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