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Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Progress in the Development of Pyrophosphate Bioisosteres: Synthesis and Biomedical Potential of 1-Fluoro- and 1,1-Difluoromethylene-1,1-bisphosphonates

Author(s): Vadim D. Romanenko and Valery P. Kukhar

Volume 18, Issue 11, 2014

Page: [1491 - 1512] Pages: 22

DOI: 10.2174/138527281811140815124708

Price: $65

Abstract

Mono- and difluoromethylenebisphosphonates are of great synthetic and biological interest since they are among the best isopolar pyrophosphate mimics. This review will emphasize preparation and some of the most important applications of these compounds. The following synthetic approaches to fluoromethylenebisphosphonates are summarized: (i) electrophilic halogenation, (ii) Arbuzov and Michaelis-Becker reactions, (iii) direct electrophilic phosphorylation of fluoromethylphosphonate carbanions, and (iv) autocondensation of fluoromethylphosphonate carbanions. Emphasis is given to the synthesis and biomedical application of modified nucleoside polyphosphates, incorporating fluoromethylenebisphosphonate scaffold.

Keywords: Enzyme inhibitors, fluorinated bisphosphonates, modified nucleoside polyphosphates, phosphate mimics, synthetic methods

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