Literature DB >> 17166725

Synthesis of the 5-phosphono-pent-2-en-1-yl nucleosides: a new class of antiviral acyclic nucleoside phosphonates.

Hyunah Choo1, James R Beadle, Youhoon Chong, Julissa Trahan, Karl Y Hostetler.   

Abstract

A new class of acyclic nucleoside phosphonates, the 5-phosphono-pent-2-en-1-yl nucleosides and their hexadecyloxypropyl esters, were synthesized from butyn-1-ol. Only the hexadecyloxypropyl esters showed antiviral activity against herpes simplex virus type 1, in vitro. Hexadecyloxypropyl 1-(5-phosphono-pent-2-en-1-yl)-thymine was the most active and selective compound among the synthesized nucleotides with an EC50 value of 0.90 microM.

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Year:  2006        PMID： 17166725      PMCID： PMC1810563          DOI： 10.1016/j.bmc.2006.11.038

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  21 in total

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2.  Stereoselective synthesis and antiviral activity of D-2',3'-didehydro-2',3'-dideoxy-2'-fluoro-4'-thionucleosides.

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Review 3.  Herpes simplex virus: receptors and ligands for cell entry.

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Journal:  Cell Microbiol       Date:  2004-05       Impact factor: 3.715

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Journal:  J Virol       Date:  2003-10       Impact factor: 5.103

5.  9-(2-hydroxyethoxymethyl) guanine activity against viruses of the herpes group.

Authors:  H J Schaeffer; L Beauchamp; P de Miranda; G B Elion; D J Bauer; P Collins
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6.  Increased antiviral activity of 1-O-hexadecyloxypropyl-[2-(14)C]cidofovir in MRC-5 human lung fibroblasts is explained by unique cellular uptake and metabolism.

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Authors:  Stephanie L Ciesla; Julissa Trahan; W Brad Wan; James R Beadle; Kathy A Aldern; George R Painter; Karl Y Hostetler
Journal:  Antiviral Res       Date:  2003-08       Impact factor: 5.970

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  3 in total

Review 1.  Synthesis of nucleoside phosphate and phosphonate prodrugs.

Authors:  Ugo Pradere; Ethel C Garnier-Amblard; Steven J Coats; Franck Amblard; Raymond F Schinazi
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2.  Antiviral activities of novel 5-phosphono-pent-2-en-1-yl nucleosides and their alkoxyalkyl phosphonoesters.

Authors:  Hyunah Choo; James R Beadle; Earl R Kern; Mark N Prichard; Kathy A Keith; Caroll B Hartline; Julissa Trahan; Kathy A Aldern; Brent E Korba; Karl Y Hostetler
Journal:  Antimicrob Agents Chemother       Date:  2006-11-27       Impact factor: 5.191

3.  Alkoxyalkyl prodrugs of acyclic nucleoside phosphonates enhance oral antiviral activity and reduce toxicity: current state of the art.

Authors:  Karl Y Hostetler
Journal:  Antiviral Res       Date:  2009-05       Impact factor: 5.970
  3 in total

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