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Synthesis and antiviral evaluation of 9-(S)-[3-alkoxy-2-(phosphonomethoxy)propyl]nucleoside alkoxyalkyl esters: inhibitors of hepatitis C virus and HIV-1 replication.

Abstract：

:We reported previously that octadecyloxyethyl 9-(S)-[3-hydroxy-2-(phosphonomethoxy)-propyl]adenine (ODE-(S)-HPMPA) was active against genotype 1b and 2a hepatitis C virus (HCV) replicons. This is surprising because acyclic nucleoside phosphonates have been regarded as having antiviral activity only against double stranded DNA viruses, HIV and HBV. We synthesized octadecyloxyethyl 9-(S)-[3-methoxy-2-(phosphonomethoxy)propyl]-adenine and found it to be active in genotype 1b and 2a HCV replicons with EC₅₀ values of 1-2 μM and a CC₅₀ of > 150 μM. Analogs with substitutions at the 3'-hydroxyl larger than methyl or ethyl, or with other purine bases were less active but most compounds had significant antiviral activity against HIV-1 in vitro. The most active anti-HIV compound was octadecyloxyethyl 9-(R)-[3-methoxy-2-(phosphonomethoxy)propyl]guanine with an EC₅₀ < 0.01 nanomolar and a selectivity index of > 4.4 million.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Valiaeva N,Wyles DL,Schooley RT,Hwu JB,Beadle JR,Prichard MN,Hostetler KY

doi

10.1016/j.bmc.2011.06.009

subject

Has Abstract

pub_date

2011-08-01 00:00:00

pages

4616-25

issue

15

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(11)00437-8

journal_volume

19

pub_type

杂志文章

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