Literature DB >> 15341963

Synthesis of acyloxymethyl ester prodrugs of the transferable protein farnesyl transferase substrate farnesyl methylenediphosphonate.

Jerry M Troutman1, Kareem A H Chehade, Katarzyna Kiegiel, Douglas A Andres, H Peter Spielmann.   

Abstract

Three isoprenoid diphosphate analogues of farnesyl diphosphate (FPP) where the diphosphate has been replaced by methylene diphosphonate and the negative charges masked by frangible pivaloyloxymethyl (POM) esters were prepared. Farnesyl methylenediphosphonate is a sub-micromolar substrate for protein farnesyl transferase. The tripivaloyloxymethyl esters of isoprenoid methylenediphosphonate have significantly increased lipophilicity and may act as important farnesyl diphosphate prodrugs.

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Year:  2004        PMID: 15341963     DOI: 10.1016/j.bmcl.2004.07.017

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


  9 in total

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

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

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Journal:  Future Med Chem       Date:  2019-07       Impact factor: 3.808

Review 4.  Targeting prenylation inhibition through the mevalonate pathway.

Authors:  Pimyupa Manaswiyoungkul; Elvin D de Araujo; Patrick T Gunning
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Review 5.  Prodrugs of pyrophosphates and bisphosphonates: disguising phosphorus oxyanions.

Authors:  Emma S Rudge; Alex H Y Chan; Finian J Leeper
Journal:  RSC Med Chem       Date:  2022-03-01

6.  Synthesis of 5'-methylene-phosphonate furanonucleoside prodrugs: application to D-2'-deoxy-2'-α-fluoro-2'-β-C-methyl nucleosides.

Authors:  Ugo Pradere; Franck Amblard; Steven J Coats; Raymond F Schinazi
Journal:  Org Lett       Date:  2012-08-23       Impact factor: 6.005

7.  A new motif for inhibitors of geranylgeranyl diphosphate synthase.

Authors:  Benjamin J Foust; Cheryl Allen; Sarah A Holstein; David F Wiemer
Journal:  Bioorg Med Chem       Date:  2016-06-10       Impact factor: 3.641

8.  Evaluation of a 7-Methoxycoumarin-3-carboxylic Acid Ester Derivative as a Fluorescent, Cell-Cleavable, Phosphonate Protecting Group.

Authors:  Andrew J Wiemer; Rebekah R Shippy; Ashley M Kilcollins; Jin Li; Chia-Hung Christine Hsiao; Rocky J Barney; M Lei Geng; David F Wiemer
Journal:  Chembiochem       Date:  2015-11-19       Impact factor: 3.164

9.  Use of synthetic isoprenoids to target protein prenylation and Rho GTPases in breast cancer invasion.

Authors:  Min Chen; Teresa Knifley; Thangaiah Subramanian; H Peter Spielmann; Kathleen L O'Connor
Journal:  PLoS One       Date:  2014-02-26       Impact factor: 3.240

  9 in total

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