Study of chemical stability of antivirally active 5-azacytosine acyclic nucleoside phosphonates using NMR spectroscopy
Language English Country England, Great Britain Media print-electronic
Document type Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't
Grant support
1UC1AI062540-01
NIAID NIH HHS - United States
PubMed
18554916
DOI
10.1016/j.bmc.2008.05.058
PII: S0968-0896(08)00500-2
Knihovny.cz E-resources
- MeSH
- Antiviral Agents chemistry MeSH
- Cytosine analogs & derivatives chemistry MeSH
- Guanidines MeSH
- Hydrolysis MeSH
- Magnetic Resonance Spectroscopy MeSH
- Nucleosides chemistry MeSH
- Organophosphonates chemistry MeSH
- Drug Stability MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Research Support, N.I.H., Extramural MeSH
- Names of Substances
- 5-azacytosine MeSH Browser
- Antiviral Agents MeSH
- Cytosine MeSH
- Guanidines MeSH
- Nucleosides MeSH
- Organophosphonates MeSH
Hydrolytic decomposition of four 5-azacytosine acyclic nucleoside phosphonates was studied. Products of the decomposition are carbamoylguanidine derivatives. Stability and decomposition products of HPMP-5-azaC (a 5-azacytosine derivative with strong antiviral activity) differ from the other derivatives. The reaction pathway of HPMP-5-azaC involves a formyl derivative formed by intramolecular transformylation reaction.
References provided by Crossref.org
Phosphonates and Phosphonate Prodrugs in Medicinal Chemistry: Past Successes and Future Prospects
Synthesis of fluorinated acyclic nucleoside phosphonates with 5-azacytosine base moiety
New prodrugs of two pyrimidine acyclic nucleoside phosphonates: Synthesis and antiviral activity
