Synthesis and anti-HIV evaluation of new acyclic phosphonate nucleotide analogues and their bis(SATE) derivatives.

This article describes a very simple route for synthesizing novel lipophilic phosphonate bis(t-bu-SATE) prodrugs of acyclic cyclopentenylated nucleosides such as adenine 17 and cytosine 18. The key intermediate 6 was constructed via a ring-closing metathesis of compound 5, which could be readily prepared from diethylmalonate 4. The chemical stability of the bis(SATE) derivatives was tested at neutral (pH = 7.2) and slightly acid (milli-Q water, pH = 5.5) pH. The synthesized compounds were evaluated as potential antiviral agents against HIV-1 virus.

Citation

Hua Li, Joon Hee Hong. Synthesis and anti-HIV evaluation of new acyclic phosphonate nucleotide analogues and their bis(SATE) derivatives. Nucleosides, nucleotides & nucleic acids. 2010 Aug;29(8):581-90

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PMID: 20661812

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