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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Current Organic Chemistry
Title:Progress in the Development of Pyrophosphate Bioisosteres: Synthesis and Biomedical Potential of 1-Fluoro- and 1,1-Difluoromethylene-1,1-bisphosphonates
Volume: 18 Issue: 11
Author(s): Vadim D. Romanenko and Valery P. Kukhar
Affiliation:
Keywords: Enzyme inhibitors, fluorinated bisphosphonates, modified nucleoside polyphosphates, phosphate mimics, synthetic methods
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.
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Cite this article as:
Romanenko D. Vadim and Kukhar P. Valery, Progress in the Development of Pyrophosphate Bioisosteres: Synthesis and Biomedical Potential of 1-Fluoro- and 1,1-Difluoromethylene-1,1-bisphosphonates, Current Organic Chemistry 2014; 18 (11) . https://dx.doi.org/10.2174/138527281811140815124708
DOI https://dx.doi.org/10.2174/138527281811140815124708 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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