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 |
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MDPI AG
2020-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/17/3865 |
| _version_ | 1797555673361285120 |
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| author | Qi Chen Stewart W. Schneller Chong Liu Kathryn L. Jones Tyler Singer |
| author_facet | Qi Chen Stewart W. Schneller Chong Liu Kathryn L. Jones Tyler Singer |
| author_sort | Qi Chen |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-10T16:50:51Z |
| format | Article |
| id | doaj.art-81bf9e0849de481ab6d8df0dc5bfce7e |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T16:50:51Z |
| publishDate | 2020-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-81bf9e0849de481ab6d8df0dc5bfce7e2023-11-20T11:18:58ZengMDPI AGMolecules1420-30492020-08-012517386510.3390/molecules251738655′-Nor-3-Deaza-1′,6′-Isoneplanocin, the Synthesis and Antiviral StudyQi Chen0Stewart W. Schneller1Chong Liu2Kathryn L. Jones3Tyler Singer4Department of Chemistry, Slippery Rock University, Slippery Rock, PA 16057, USAMolette Laboratory for Drug Discovery, Department of Chemistry and Biochemistry, Auburn, Auburn University, Auburn, AL 36849, USAMolette Laboratory for Drug Discovery, Department of Chemistry and Biochemistry, Auburn, Auburn University, Auburn, AL 36849, USADepartment of Chemistry, Slippery Rock University, Slippery Rock, PA 16057, USADepartment of Chemistry, Slippery Rock University, Slippery Rock, PA 16057, USAThe 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.https://www.mdpi.com/1420-3049/25/17/3865antiviralscarbocyclic nucleosidesneplanocinUllmann reaction |
| spellingShingle | Qi Chen Stewart W. Schneller Chong Liu Kathryn L. Jones Tyler Singer 5′-Nor-3-Deaza-1′,6′-Isoneplanocin, the Synthesis and Antiviral Study Molecules antivirals carbocyclic nucleosides neplanocin Ullmann reaction |
| title | 5′-Nor-3-Deaza-1′,6′-Isoneplanocin, the Synthesis and Antiviral Study |
| title_full | 5′-Nor-3-Deaza-1′,6′-Isoneplanocin, the Synthesis and Antiviral Study |
| title_fullStr | 5′-Nor-3-Deaza-1′,6′-Isoneplanocin, the Synthesis and Antiviral Study |
| title_full_unstemmed | 5′-Nor-3-Deaza-1′,6′-Isoneplanocin, the Synthesis and Antiviral Study |
| title_short | 5′-Nor-3-Deaza-1′,6′-Isoneplanocin, the Synthesis and Antiviral Study |
| title_sort | 5 nor 3 deaza 1 6 isoneplanocin the synthesis and antiviral study |
| topic | antivirals carbocyclic nucleosides neplanocin Ullmann reaction |
| url | https://www.mdpi.com/1420-3049/25/17/3865 |
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