Issue 44, 2019

2,4-Substituted bispidines as rigid hosts for versatile applications: from κ-opioid receptor to metal coordination

Abstract

Bispidones (3,7-diazabicyclo[3.3.1]nonan-9-one) are bicyclic analogues of the natural antiarrhythmic agent, spartein. They can straightforwardly be obtained from two successive Mannich reactions. Reduction of the ketone gives the corresponding bispidol. Substituted bispidones and bispidols offer a large playground by varying the substituents, the configuration of the carbon atoms in position 2 and 4 as well as the conformation of the bicycle. While chair–boat conformers display a strong affinity for κ-opioid receptors, chair–chair bispidines provide adaptable coordination spheres for transition metal and rare-earth ions. Because of their very rich coordination chemistry, substituted bispidines have emerged in various applications of coordination chemistry, such as catalysis, magnetism and medical imaging.

Graphical abstract: 2,4-Substituted bispidines as rigid hosts for versatile applications: from κ-opioid receptor to metal coordination

Article information

Article type
Perspective
Submitted
27 aug 2019
Accepted
04 okt 2019
First published
04 okt 2019

Dalton Trans., 2019,48, 16476-16492

2,4-Substituted bispidines as rigid hosts for versatile applications: from κ-opioid receptor to metal coordination

A. M. Nonat, A. Roux, M. Sy and L. J. Charbonnière, Dalton Trans., 2019, 48, 16476 DOI: 10.1039/C9DT03480C

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