Title: Synthesis and antiviral activity of N(9)-[3-fluoro-2-(phosphonomethoxy)propyl] analogues derived from N(6)-substituted adenines and 2,6-diaminopurines
Authors: Baszczyňski, Ondřej ×
Jansa, Petr
Dračínský, Martin
Klepetářová, Blanka
Holý, Antonín
Votruba, Ivan
De Clercq, Erik
Balzarini, Jan
Janeba, Zlatko #
Issue Date: Apr-2011
Publisher: Pergamon
Series Title: Bioorganic & Medicinal Chemistry vol:19 issue:7 pages:2114-24
Abstract: 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.
ISSN: 0968-0896
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Laboratory of Virology and Chemotherapy (Rega Institute)
× corresponding author
# (joint) last author

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