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Synthesis of Cryptophane-223-Type Derivatives with Dual Functionalization.

Authors :
Baydoun O
De Rycke N
Léonce E
Boutin C
Berthault P
Jeanneau E
Brotin T
Source :
The Journal of organic chemistry [J Org Chem] 2019 Jul 19; Vol. 84 (14), pp. 9127-9137. Date of Electronic Publication: 2019 Jul 05.
Publication Year :
2019

Abstract

In this article, we present the synthesis of new cryptophane-type hosts capable of binding xenon in aqueous media and that may be useful for the development of xenon-based magnetic resonance imaging derivatives. The synthetic route proposed was chosen to facilitate both the introduction of water-solubilizing substituents and the functionalization of the host with a single arm showing recognition properties that constitute two crucial steps. This was made possible by preparing new cryptophane-223 derivatives bearing two different chemical functions that can be easily modified at a later stage. Thus, subsequent reactions allowed the design of a new cryptophane host able to bind zinc or nickel cations. The ability of this molecule to bind cationic species was assessed by calorimetric titration experiments and hyperpolarized <superscript>129</superscript> Xe NMR. The advantages and disadvantages of this approach are discussed.

Details

Language :
English
ISSN :
1520-6904
Volume :
84
Issue :
14
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
31246016
Full Text :
https://doi.org/10.1021/acs.joc.9b01093