Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 19, Issue 7, Pages 2114-2124Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2011.02.050
Keywords
Acyclic nucleoside phosphonates; Purines; FPMP; Antiviral; N-6-Methyl-AMP aminohydrolase
Funding
- Institute of Organic Chemistry and Biochemistry, v.v.i. [OZ40550506]
- Center of new antivirals and antineoplastics [1M0508]
- Ministry of Education, Youth and Sports of the Czech Republic
- Gilead Sciences and the IOCB Research Center
- K.U. Leuven [GOA 10/014]
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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. (C) 2011 Elsevier Ltd. All rights reserved.
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