Nitrile Containing Bisphosphonates: Easy Synthesis through Metal Catalyzed Michael Addition
| Autor: | Giorgio Strukul, Martina Damuzzo, Andrea Chiminazzo, Alessandro Scarso, Laura Sperni |
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| Rok vydání: | 2017 |
| Předmět: |
Nitrile
010405 organic chemistry Chemistry Organic Chemistry 010402 general chemistry 01 natural sciences Biochemistry Catalysis 0104 chemical sciences Inorganic Chemistry Metal chemistry.chemical_compound visual_art Drug Discovery Amphiphile Michael reaction visual_art.visual_art_medium Organic chemistry Moiety Physical and Theoretical Chemistry Trimethylsilyl cyanide Conjugate |
| Zdroj: | Helvetica Chimica Acta. 100:e1700104 |
| ISSN: | 0018-019X |
| DOI: | 10.1002/hlca.201700104 |
| Popis: | New nitrile-containing gem-bisphosphonates as drug candidates for the contrast of osteoporosis are presented, their synthesis being based on the metal catalyzed Michael conjugate addition of trimethylsilyl cyanide to unsaturated bisphosphonate precursors. Zn(OTf)2 turned out to be the most efficient metal catalyst for the reaction enabling the formation of β-nitrile substituted bisphosphonates in good yields. The corresponding final bisphosphonic acids bearing the nitrile moiety were obtained by deprotection of the ethyl ester moiety. They showed aggregation properties in water due to their amphiphilic nature and will be evaluated in order to assess their biological anti-osteoclast activity. This article is protected by copyright. All rights reserved. |
| Databáze: | OpenAIRE |
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