Literature DB >> 17459701

Bis[(para-methoxy)benzyl] phosphonate prodrugs with improved stability and enhanced cell penetration.

Qun Dang1, Yan Liu, Robert M Rydzewski, Brian S Brown, Edward Robinson, Paul D van Poelje, Timothy J Colby, Mark D Erion.   

Abstract

A series of substituted bis[(para-methoxy)benzyl] (bisPMB) esters of 1-naphthalenemethylphosphonate (NMPA) were synthesized and evaluated as phosphonate prodrugs. BisPMB NMPA esters (4b and 4c) with significantly improved aqueous stability were identified that also resulted in increased intracellular levels of NMPA following prodrug incubation with primary rat hepatocytes.

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Year:  2007        PMID: 17459701     DOI: 10.1016/j.bmcl.2007.03.089

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


  3 in total

Review 1.  Prodrugs of phosphonates and phosphates: crossing the membrane barrier.

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

Review 2.  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

3.  Preparation and Applications of 4-Methoxybenzyl Esters in Organic Synthesis.

Authors:  Kyle T Howard; John D Chisholm
Journal:  Org Prep Proced Int       Date:  2016-01-29       Impact factor: 1.628

  3 in total

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