5′-Nor-3-Deaza-1′,6′-Isoneplanocin, the Synthesis and Antiviral Study
The arbocyclic nucleosides aristeromycin and neplanocin have been studied as a source for new antiviral agents. A convenient synthesis of C-5′-truncated 3-deaza-1′,6′-isoneplanocin, which combines the features of antiviral candidates 5′-noraristeromycin and 3-deaza-1′,6′-isoneplanocin is reported fr...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2020-08-01
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| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/25/17/3865 |
| Summary: | The arbocyclic nucleosides aristeromycin and neplanocin have been studied as a source for new antiviral agents. A convenient synthesis of C-5′-truncated 3-deaza-1′,6′-isoneplanocin, which combines the features of antiviral candidates 5′-noraristeromycin and 3-deaza-1′,6′-isoneplanocin is reported from (−)-cyclopentenone to give the two C-4′ epimers of 5′-nor-3-deaza isoneplanocin. Antiviral assays showed activity against the JC virus (EC<sub>50</sub> = 1.12 µM for (4′<i>R</i>)-<b>8</b>; EC<sub>50</sub> = 59.14 µM for (4′<i>S</i>)-<b>7</b>) and inactivity of both compounds against several DNA and RNA viruses. Both compounds lacked cytotoxicity. |
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| ISSN: | 1420-3049 |