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3,7-Dideazaneplanocin: Synthesis and antiviral analysis
| Content Provider | Semantic Scholar |
|---|---|
| Author | Yin, Xue-qiang Schneller, Stewart W. |
| Copyright Year | 2017 |
| Abstract | Objective To synthesize 3,7-dideazaneplanocin and evaluate its antiviral potential. Methods The target 3,7-dideazaneplanocin has been prepared in five steps from a readily available cyclopentenol. A thorough in vitro antiviral analysis was conducted versus both DNA and RNA viruses. Results A rational synthesis of 3,7-dideazaneplanocin was conceived and successfully pursued in such a way that it can be adapted to various analogs of 3,7-dideazaneplanocin. Using standard antiviral assays, no activity for 3,7-dideazaneplanocn was found. Conclusion Two structural features are necessary for adenine-based carbocyclic nucleosides (like neplanocin) for potential antiviral properties: (i) inhibition of S-adenosylhomocysteine hydrolase and/or (ii) C-5' activation via the mono-nucleotide. These two requisite adenine structural features to fit these criteria are not present in in the target 3,7-dideazaneplanocin: (i) an N-7 is necessary for inhibition of the hydrolase and the N-3 is claimed to be essential for phosphorylation at C-5'. Thus, it is not surprising that 3,7-dideazaneplaoncin lacked antiviral properties. |
| Starting Page | 90 |
| Ending Page | 93 |
| Page Count | 4 |
| File Format | PDF HTM / HTML |
| PubMed reference number | 29172646v1 |
| Alternate Webpage(s) | https://doi.org/10.1177/2040206617742561 |
| DOI | 10.1177/2040206617742561 |
| Journal | Antiviral chemistry & chemotherapy |
| Volume Number | 25 |
| Language | English |
| Access Restriction | Open |
| Subject Keyword | Adenine Analog Antiviral Agents Hydrolase Nucleotides Purine Nucleosides RNA Viruses S-Adenosylhomocysteine Virus neplanocin A |
| Content Type | Text |
| Resource Type | Article |
