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Synthesis and antiviral activity of N9-[3-fluoro-2-(phosphonomethoxy)propyl] analogues derived from N6-substituted adenines and 2,6-diaminopurines
O. Baszczyňski, P. Jansa, M. Dračínský, B. Klepetářová, A. Holý, I. Votruba, E. de Clercq, J. Balzarini, Z. Janeba,
Language English Country England, Great Britain
Document type Journal Article, Research Support, Non-U.S. Gov't
- 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
- Phosphorous Acids chemical synthesis chemistry pharmacology MeSH
- Humans MeSH
- Moloney murine sarcoma virus drug effects MeSH
- Mice, Inbred C3H MeSH
- Mice 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
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
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