Literature DB >> 11327587

Synthesis and evaluation of novel amidate prodrugs of PMEA and PMPA.

C Ballatore1, C McGuigan, E De Clercq, J Balzarini.   

Abstract

Some novel amidate prodrugs of PMEA and PMPA have been synthesised and tested in vitro for their biological activity. Compound 5 in particular showed greatly enhanced antiviral potency compared with the parent nucleotide analogue. In vitro enzymatic studies and structure-activity relationships indicate that the degradation mechanism of such prodrugs may be the same as that described for the phosphoramidate triesters of nucleotide analogues.

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Year:  2001        PMID: 11327587     DOI: 10.1016/s0960-894x(01)00128-7

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  12 in total

1.  Chain-terminating dinucleoside tetraphosphates are substrates for DNA polymerization by human immunodeficiency virus type 1 reverse transcriptase with increased activity against thymidine analogue-resistant mutants.

Authors:  Peter R Meyer; Anthony J Smith; Suzanne E Matsuura; Walter A Scott
Journal:  Antimicrob Agents Chemother       Date:  2006-08-28       Impact factor: 5.191

Review 2.  Prodrugs of phosphonates and phosphates: crossing the membrane barrier.

Authors:  Andrew J Wiemer; David F Wiemer
Journal:  Top Curr Chem       Date:  2015

Review 3.  Phosphonate prodrugs: an overview and recent advances.

Authors:  Kenneth M Heidel; Cynthia S Dowd
Journal:  Future Med Chem       Date:  2019-07       Impact factor: 3.808

Review 4.  Synthesis of nucleoside phosphate and phosphonate prodrugs.

Authors:  Ugo Pradere; Ethel C Garnier-Amblard; Steven J Coats; Franck Amblard; Raymond F Schinazi
Journal:  Chem Rev       Date:  2014-08-21       Impact factor: 60.622

Review 5.  The expanding role of prodrugs in contemporary drug design and development.

Authors:  Jarkko Rautio; Nicholas A Meanwell; Li Di; Michael J Hageman
Journal:  Nat Rev Drug Discov       Date:  2018-04-27       Impact factor: 84.694

6.  Synthesis and biological activation of an ethylene glycol-linked amino acid conjugate of cyclic cidofovir.

Authors:  Ulrika Eriksson; John M Hilfinger; Jae-Seung Kim; Stefanie Mitchell; Paul Kijek; Katherine Z Borysko; Julie M Breitenbach; John C Drach; Boris A Kashemirov; Charles E McKenna
Journal:  Bioorg Med Chem Lett       Date:  2006-11-10       Impact factor: 2.823

Review 7.  Prodrug approaches to improving the oral absorption of antiviral nucleotide analogues.

Authors:  Larryn W Peterson; Charles E McKenna
Journal:  Expert Opin Drug Deliv       Date:  2009-04       Impact factor: 6.648

8.  Serine peptide phosphoester prodrugs of cyclic cidofovir: synthesis, transport, and antiviral activity.

Authors:  Ulrika Eriksson; Larryn W Peterson; Boris A Kashemirov; John M Hilfinger; John C Drach; Katherine Z Borysko; Julie M Breitenbach; Jae Seung Kim; Stefanie Mitchell; Paul Kijek; Charles E McKenna
Journal:  Mol Pharm       Date:  2008-05-16       Impact factor: 4.939

9.  Evaluation of nucleoside phosphonates and their analogs and prodrugs for inhibition of orthopoxvirus replication.

Authors:  Kathy A Keith; Michael J M Hitchcock; William A Lee; Antonin Holý; Earl R Kern
Journal:  Antimicrob Agents Chemother       Date:  2003-07       Impact factor: 5.191

Review 10.  Adenine: an important drug scaffold for the design of antiviral agents.

Authors:  Changyuan Wang; Zhendong Song; Haiqing Yu; Kexin Liu; Xiaodong Ma
Journal:  Acta Pharm Sin B       Date:  2015-09-02       Impact factor: 11.413

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