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Antiviral activity of cyclopentenyl nucleosides against orthopox viruses (Smallpox, monkeypox and cowpox)

An improved method for the synthesis of enantiomerically pure d-cyclopentenyl nucleosides has been accomplished and their antiviral activity against orthopox viruses have been evaluated. The key intermediate, l-cyclopent-2-enone 13 was prepared from d-ribose using a ring closing metathesis reaction...

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Detalles Bibliográficos
Autores principales: Chu, C.K, Jin, Y.H, Baker, R.O, Huggins, J
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier Science Ltd. 2003
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9628949/
https://www.ncbi.nlm.nih.gov/pubmed/12467606
http://dx.doi.org/10.1016/S0960-894X(02)00841-7
Descripción
Sumario:An improved method for the synthesis of enantiomerically pure d-cyclopentenyl nucleosides has been accomplished and their antiviral activity against orthopox viruses have been evaluated. The key intermediate, l-cyclopent-2-enone 13 was prepared from d-ribose using a ring closing metathesis reaction in eight steps. Among the synthesized nucleosides, the adenine 2 (Neplanocin A), cytosine 14, and 5-F-cytosine 15 analogues exhibited potent anti-orthopox virus activity, including smallpox virus.