Literature DB >> 1332606

Synthesis and in vitro evaluation of a phosphonate prodrug: bis(pivaloyloxymethyl) 9-(2-phosphonylmethoxyethyl)adenine.

J E Starrett1, D R Tortolani, M J Hitchcock, J C Martin, M M Mansuri.   

Abstract

9-(2-Phosphonylmethoxyethyl)adenine (PMEA; 1) was acylated with chloromethyl pivalate to afford bis(pivaloyloxymethyl) PMEA (2). The ester prodrug demonstrated enhanced in vitro potency against HSV-2 greater than 150-fold higher than the parent compound. The antiviral activity of 2 was 50-fold better than PMEA against HSV-1, and equipotent against HIV and HCMV. The toxicity of 2 was studied in both resting and growing cells.

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Year:  1992        PMID： 1332606     DOI： 10.1016/0166-3542(92)90084-i

Source DB:  PubMed          Journal:  Antiviral Res        ISSN： 0166-3542            Impact factor:   5.970


  24 in total

Review 1.  Antiviral therapy for human immunodeficiency virus infections.

Authors:  E De Clercq
Journal:  Clin Microbiol Rev       Date:  1995-04       Impact factor: 26.132

Review 2.  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 3.  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

Review 4.  Adefovir dipivoxil.

Authors:  S Noble; K L Goa
Journal:  Drugs       Date:  1999-09       Impact factor: 9.546

5.  Antiretroviral activity and pharmacokinetics in mice of oral bis(pivaloyloxymethyl)-9-(2-phosphonylmethoxyethyl)adenine, the bis(pivaloyloxymethyl) ester prodrug of 9-(2-phosphonylmethoxyethyl)adenine.

Authors:  L Naesens; J Balzarini; N Bischofberger; E De Clercq
Journal:  Antimicrob Agents Chemother       Date:  1996-01       Impact factor: 5.191

Review 6.  Alpha-carboxynucleoside phosphonates: direct-acting inhibitors of viral DNA polymerases.

Authors:  Jan Balzarini; Alan Ford; Nuala M Maguire; Jubi John; Kalyan Das; Eddy Arnold; Wim Dehaen; Anita Maguire
Journal:  Future Med Chem       Date:  2019-01-16       Impact factor: 3.808

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

8.  Inhibition of duck hepatitis B virus replication by 9-(2-phosphonylmethoxyethyl)adenine, an acyclic phosphonate nucleoside analogue.

Authors:  A J Nicoll; D L Colledge; J J Toole; P W Angus; R A Smallwood; S A Locarnini
Journal:  Antimicrob Agents Chemother       Date:  1998-12       Impact factor: 5.191

9.  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

10.  Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models.

Authors:  Sophie Duraffour; Robert Snoeck; Marcela Krecmerová; Joost van Den Oord; Rita De Vos; Antonín Holy; Jean-Marc Crance; Daniel Garin; Erik De Clercq; Graciela Andrei
Journal:  Antimicrob Agents Chemother       Date:  2007-09-24       Impact factor: 5.191
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