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Issue 11, 2014
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Synthesis of α-brominated phosphonates and their application as phosphate bioisosteres

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Abstract

Substrate phosphorylation is a key modulator of signal transduction. Abnormal phosphorylation in vivo is implicated in many diseases including cancer, diabetes, and Alzheimer's disease. Inhibitors of phosphate-recognizing proteins have potential as medicinal agents as well as tools to study phosphorylation pathways. A well-known and common inhibition strategy is to synthetically replace the labile phosphate moiety with a non-hydrolyzable phosphonate. Fully saturated, α-fluoro and α,α-difluorophosphonates are often effective phosphate bioisosteres and have been well studied. More recently α-brominated phosphonates have begun to emerge as inhibitors of phosphate recognizing enzymes, some of which operate by irreversible mechanisms. Herein we discuss the synthetic approaches to aliphatic and benzylic α-bromophosphonates and their biological activities.

Graphical abstract: Synthesis of α-brominated phosphonates and their application as phosphate bioisosteres

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Article information


Submitted
13 Jun 2014
Accepted
07 Aug 2014
First published
05 Sep 2014

This article is Open Access

Med. Chem. Commun., 2014,5, 1619-1633
Article type
Review Article
Author version available

Synthesis of α-brominated phosphonates and their application as phosphate bioisosteres

A. M. Downey and C. W. Cairo, Med. Chem. Commun., 2014, 5, 1619
DOI: 10.1039/C4MD00255E

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