Synthesis and antiviral activity of N9-[3-fluoro-2-(phosphonomethoxy)propyl] analogues derived from N6-substituted adenines and 2,6-diaminopurines
Language English Country Great Britain, England Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
21429755
DOI
10.1016/j.bmc.2011.02.050
PII: S0968-0896(11)00168-4
Knihovny.cz E-resources
- MeSH
- 2-Aminopurine analogs & derivatives chemical synthesis chemistry pharmacology MeSH
- Adenine analogs & derivatives chemical synthesis chemistry pharmacology MeSH
- Antiviral Agents chemical synthesis chemistry pharmacology MeSH
- 3T3 Cells MeSH
- HIV-1 drug effects MeSH
- HIV-2 drug effects MeSH
- Crystallography, X-Ray MeSH
- Cells, Cultured MeSH
- Humans MeSH
- Moloney murine sarcoma virus drug effects MeSH
- Mice, Inbred C3H MeSH
- Mice MeSH
- Organophosphonates chemical synthesis chemistry pharmacology MeSH
- Purines chemical synthesis chemistry pharmacology MeSH
- Dose-Response Relationship, Drug MeSH
- Structure-Activity Relationship MeSH
- Animals MeSH
- Check Tag
- Humans MeSH
- Mice MeSH
- Animals MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- 2-Aminopurine MeSH
- 2,6-diaminopurine MeSH Browser
- Adenine MeSH
- Antiviral Agents MeSH
- Organophosphonates MeSH
- Purines MeSH
An efficient method for the synthesis of N(9)-[3-fluoro-2-(phosphonomethoxy)propyl] (FPMP) derivatives of purine bases has been developed. Both (R)- and (S)-enantiomers of the N(6)-substituted FPMP derivatives of adenine and 2,6-diaminopurine were prepared and their anti-human immunodeficiency virus (HIV) and anti-Moloney murine sarcoma virus (MSV) activity was evaluated. Whereas none of the 6-substituted FPMPA derivatives showed any antiviral activity, several FPMPDAP derivatives had a moderate antiretroviral activity. Moreover, the data obtained from the study of the substrate activity of the active derivatives towards N(6)-methyl-AMP aminohydrolase support the notion that the studied N(6)-substituted FPMPDAP derivatives act as prodrugs of the antiretroviral FPMPG analogues.
References provided by Crossref.org
Synthesis of fluorinated acyclic nucleoside phosphonates with 5-azacytosine base moiety
