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Discovery and Synthesis of a Phosphoramidate Prodrug of a Pyrrolo[2,1-f][triazin-4-amino] Adenine C-Nucleoside (GS-5734) for the Treatment of Ebola and Emerging Viruses
Open accessAbstract
= 86 nM in macrophages as the clinical candidate. Structure activity relationships established that the 1'-CN group and C-linked nucleobase were critical for optimal anti-EBOV potency and selectivity against host polymerases. A robust diastereoselective synthesis provided sufficient quantities of 4b to enable preclinical efficacy in a non-human-primate EBOV challenge model. Once-daily 10 mg/kg iv treatment on days 3-14 postinfection had a significant effect on viremia and mortality, resulting in 100% survival of infected treated animals [ Nature 2016 , 531 , 381 - 385 ]. A phase 2 study (PREVAIL IV) is currently enrolling and will evaluate the effect of 4b on viral shedding from sanctuary sites in EBOV survivors.
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Metadata
- Authors
- Siegel, D., Hui, H. C., Doerffler, E., Clarke, M. O., Chun, K., Zhang, L., Neville, S., Carra, E., Lew, W., Ross, B., Wang, Q., Wolfe, L., Jordan, R., Soloveva, V., Knox, J., Perry, J., Perron, M., Stray, K. M., Barauskas, O., Feng, J. Y., Xu, Y., Lee, G., Rheingold, A. L., Ray, A. S., Bannister, R., Strickley, R., Swaminathan, S., Lee, W. A., Bavari, S., Cihlar, T., Lo, M. K., Warren, T. K., & Mackman, R. L.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2017-01-26
- Volume
- 60
- Issue
- 5
- Pages
- 1648-1661
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2581273760
- Cited by
- 643
- References
- 0
- Type
- other
- Language
- en
- Open access
- green
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- CoChat. (2026). Citation check: Discovery and Synthesis of a Phosphoramidate Prodrug of a Pyrrolo[2,1-f][triazin-4-amino] Adenine C-Nucleoside (GS-5734) for the Treatment of Ebola and Emerging Viruses. https://app.cochat.ai/papers/10.1021/acs.jmedchem.6b01594
- The paper
- Siegel, D., Hui, H. C., Doerffler, E., Clarke, M. O., Chun, K., Zhang, L., Neville, S., Carra, E., Lew, W., Ross, B., Wang, Q., Wolfe, L., Jordan, R., Soloveva, V., Knox, J., Perry, J., Perron, M., Stray, K. M., Barauskas, O., . . . Mackman, R. L. (2017). Discovery and Synthesis of a Phosphoramidate Prodrug of a Pyrrolo[2,1-f][triazin-4-amino] Adenine C-Nucleoside (GS-5734) for the Treatment of Ebola and Emerging Viruses. Journal of Medicinal Chemistry. https://doi.org/10.1021/acs.jmedchem.6b01594
Data sources
Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
