Literature DB >> 14529543

Phosphonomethoxyalkyl analogs of nucleotides.

Antonín Holy1.   

Abstract

Acyclic nucleoside phosphonates (ANP) are analogs of nucleotides exhibiting various biological (e.g. antiviral, cytostatic, antiparasitic, immunomodulatory) activities. This review describes synthetic approaches to their preparation, biological activities, structure-activity relationships and mode of action of ANPs, with emphasis to selected drugs or drug candidates. Three compounds of the ANP group (cidofovir, adefovir, tenofovir) are active components of potent antivirals approved for therapeutic use in human medicine aimed at hepatitis B, AIDS and various diseases caused by DNA viruses.

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Year:  2003        PMID： 14529543     DOI： 10.2174/1381612033453668

Source DB:  PubMed          Journal:  Curr Pharm Des        ISSN： 1381-6128            Impact factor:   3.116


  37 in total

1.  Tyrosine-based 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine and -adenine ((S)-HPMPC and (S)-HPMPA) prodrugs: synthesis, stability, antiviral activity, and in vivo transport studies.

Authors:  Valeria M Zakharova; Michaela Serpi; Ivan S Krylov; Larryn W Peterson; Julie M Breitenbach; Katherine Z Borysko; John C Drach; Mindy Collins; John M Hilfinger; Boris A Kashemirov; Charles E McKenna
Journal:  J Med Chem       Date:  2011-08-03       Impact factor: 7.446

2.  Alkoxyalkyl esters of (S)-9-[3-hydroxy-2-(phosphonomethoxy)propyl]adenine are potent inhibitors of the replication of wild-type and drug-resistant human immunodeficiency virus type 1 in vitro.

Authors:  Karl Y Hostetler; Kathy A Aldern; William B Wan; Stephanie L Ciesla; James R Beadle
Journal:  Antimicrob Agents Chemother       Date:  2006-08       Impact factor: 5.191

3.  Activities of acyclic nucleoside phosphonates against Orf virus in human and ovine cell monolayers and organotypic ovine raft cultures.

Authors:  F Dal Pozzo; G Andrei; A Holy; J Van Den Oord; A Scagliarini; E De Clercq; R Snoeck
Journal:  Antimicrob Agents Chemother       Date:  2005-12       Impact factor: 5.191

4.  Enhanced topical and transdermal delivery of antineoplastic and antiviral acyclic nucleoside phosphonate cPr-PMEDAP.

Authors:  Kateřina Vávrová; Petra Kovaříková; Barbora Skolová; Martina Líbalová; Jaroslav Roh; Robert Cáp; Antonín Holý; Alexandr Hrabálek
Journal:  Pharm Res       Date:  2011-06-14       Impact factor: 4.200

5.  Novel acyclic nucleoside phosphonate analogues with potent anti-hepatitis B virus activities.

Authors:  C Ying; A Holy; D Hocková; Z Havlas; E De Clercq; J Neyts
Journal:  Antimicrob Agents Chemother       Date:  2005-03       Impact factor: 5.191

6.  Approaches to tyrosine-linked peptidomimetic prodrugs of (S)-HPMP-based acyclic nucleoside phosphonates.

Authors:  Valeria M Zakharova; Ivan S Krylov; Michaela Serpi; Boris A Kashemirov; Charles E McKenna
Journal:  Phosphorus Sulfur Silicon Relat Elem       Date:  2011

7.  Acyclic nucleoside bisphosphonates: synthesis and properties of chiral 2-amino-4,6-bis[(phosphonomethoxy)alkoxy]pyrimidines.

Authors:  Petra Doláková; Martin Dracínský; Milena Masojídková; Veronika Solínová; Václav Kasicka; Antonín Holý
Journal:  Eur J Med Chem       Date:  2008-10-02       Impact factor: 6.514

Review 8.  Comparison of the π-stacking properties of purine versus pyrimidine residues. Some generalizations regarding selectivity.

Authors:  Astrid Sigel; Bert P Operschall; Helmut Sigel
Journal:  J Biol Inorg Chem       Date:  2014-01-25       Impact factor: 3.358

9.  The octadecyloxyethyl ester of (S)-9-[3-hydroxy-2-(phosphonomethoxy) propyl]adenine is a potent and selective inhibitor of hepatitis C virus replication in genotype 1A, 1B, and 2A replicons.

Authors:  David L Wyles; Kelly A Kaihara; Brent E Korba; Robert T Schooley; James R Beadle; Karl Y Hostetler
Journal:  Antimicrob Agents Chemother       Date:  2009-03-16       Impact factor: 5.191

10.  Evolution of an amino acid based prodrug approach: stay tuned.

Authors:  Ivan S Krylov; Boris A Kashemirov; John M Hilfinger; Charles E McKenna
Journal:  Mol Pharm       Date:  2013-01-22       Impact factor: 4.939
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