Recent Advances in the Structural Modifications and Applications of Ribavirin

doi:10.6023/cjoc202601025

Abstract

Structural modification of nucleoside analogues is an important strategy for developing novel drugs. Ribavirin, as one of the representative nucleoside analogues, is a broad-spectrum antiviral nucleoside drug. However, its prolonged or excessive use can lead to side effects, such as reduction in white blood cell count and inhibition of red blood cell production. Therefore, extensive research has focused on developing ribavirin derivatives with improved efficacy and reduced toxicity. This review systematically summarizes the structural modifications and applications of ribavirin, primarily including glycosyl modifications and base modifications. Additionally, novel synthetic methods and potential applications in drug development are discussed, providing insights for the development of novel antiviral drugs.

Key words: Ribavirin, structural modification, application, glycosyl modification, base modification

Cite this article

Jie Lv, Tingting Li. Recent Advances in the Structural Modifications and Applications of Ribavirin[J]. Chinese Journal of Organic Chemistry, 2026, 46(8): 3012-3024.

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Fig. & Tab. 27

Figure 1. Significance of nucleoside modification and structural modification of ribavirin

Figure 2. Glycosyl modification of ribavirin

Figure 3. Synthesis of 5-O-β-D-glucopyranosyl derivatives of ribavirin

Figure 4. CAL-B catalyzed 5-OH selective acylation reaction of ribavirin

Figure 5. 3-Step synthesis of 5-O-substituted ribavirin deri- vatives

Figure 6. CAL-B catalyzed one-step synthesis of 5-O-acylated ribavirin derivatives

Figure 7. CAL-B catalyzed synthesis of high yield 5-O-acylated vinyl ester

Figure 8. Synthesis and biological activity of hemoglobin-riba- virin conjugate

Figure 9. Synthesis of drug derivatives catalyzed by CAL-B

Figure 10. Synthesis of 5-O-phosphoramidates of ribavirin

Figure 11. Synthesis of 5-O-phosphoramidate ribavirin deri- vatives

Figure 12. Enzymatic synthesis of 5-O-acylated ribavirin esters by transesterification

Figure 13. Synthesis of L-amino acid ester prodrugs of ribavirin

Figure 14. Synthesis of macromolecular prodrugs of ribavirin

Figure 15. Synthesis of ribavirin-L-Val-glycochenodeoxy-cholic acid (GCDCA)

Figure 16. NHC/Boric acid catalysis for the synthesis of 5-O- acylated ribavirin derivatives

Figure 17. NHC catalysis for the synthesis of 3-O-acylated ribavirin derivatives

Figure 18. Modification of the 2-OH group of ribavirin

Figure 19. Synthesis of the 2-OH group modified ribavirin derivative

Figure 20. Synthesis of 2,3-O-acylated ribavirin derivatives

Figure 21. Synthesis of 2,3,5-O-modified ribavirin derivatives

Figure 22. Base modification of ribavirin

Figure 23. Synthesis of imine-modified ribavirin derivatives

Figure 24. Synthesis of azide-modified ribavirin derivatives

Figure 25. Synthesis of 5-aryltriazole ribonucleosides

Figure 26. Synthesis of alkyne-modified ribavirin derivatives

Figure 27. Synthesis of hydrazide-modified ribavirin derivatives

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