Advances in Organic Synthesis

Volume: 12

Advances in the Synthesis of Functional α-Organyl gem-Bisphosphonates for Biomedical Applications

Author(s): Vadim D. Romanenko

Pp: 200-252 (53)

DOI: 10.2174/9781681086804118120007

* (Excluding Mailing and Handling)

Abstract

This chapter deals with the synthesis of α-organyl-substituted methylenebisphosphonates and focuses on compounds not having the heteroatomic substituents at the geminal carbon. We present different methodologies on the basis of the reactivity of monophosphonate and methylene 1,1-bisphosphonate systems including the Michaelis-Arbuzov and Michaelis-Becker reactions, substitutions, Michael additions, cycloaddition, as well as more specific approaches. Together with the synthetic methods, the biomedical application of the compounds is also described.


Keywords: Alkenylidene-1, 1-Bisphosphonates, Alkylation, Anti-Inflammatory Properties, Anti-Resorption Agents, Antitumor, Asymmetric Synthesis, Bone Targeting, Bisphosphonates, Bisphosphonate Conjugates, Cycloaddition, Enzyme Inhibitors, Michaelis-Arbuzov Reaction, Michael Additions, Phosphorylation, Pyrophosphate Bioisosteres, Phosphate Mimics, Phosphonate Carbanions, Three- Component Reactions.

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