Functional bisphosphonate synthesis for the development of new anti-resorption bone drug candidates

Herein we present the synthesis of β-mono and β-bis-substituted vinylidenebisphosphonate esters bearing a carboxylic ester moiety to be used as building blocks for further functionalizations. Reactions of these new bisphosphonate scaffolds through hydrogenation of the unsaturated C&z.dbd;C bond...

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Bibliographic Details
Published inNew journal of chemistry Vol. 43; no. 32; pp. 12641 - 12649
Main Authors Bortolamiol, Enrica, Chiminazzo, Andrea, Sperni, Laura, Borsato, Giuseppe, Fabris, Fabrizio, Scarso, Alessandro
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 12.08.2019
Royal Society of Chemistry
Subjects
Aromatic compounds
Biomedical materials
Bisphosphonates
Chemistry
Chemistry, Multidisciplinary
Esters
Indoles
Osteoporosis
Physical Sciences
Science & Technology
Synthesis
CYCLOADDITION
DESIGN
POTENT
HYDROGENATION
PHOSPHONATES
INHIBITION
ANALOGS
ESTERS
X-RAY
DERIVATIVES
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Summary:Herein we present the synthesis of β-mono and β-bis-substituted vinylidenebisphosphonate esters bearing a carboxylic ester moiety to be used as building blocks for further functionalizations. Reactions of these new bisphosphonate scaffolds through hydrogenation of the unsaturated C&z.dbd;C bond and through metal mediated addition of aryl boronic acids and indoles provide a wide range of new bisphosphonate products as potential leads to contrast osteoporosis. Widening the bisphosphonate toolbox: new bisphosphonate scaffolds enable new functionalizations.
Bibliography:Electronic supplementary information (ESI) available: Full experimental procedures and characterization spectra. See DOI
10.1039/c9nj02504a
ISSN:1144-0546
1369-9261
DOI:10.1039/c9nj02504a