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

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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

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Publication details

The article was received on 27 Aug 2019, accepted on 04 Oct 2019 and first published on 04 Oct 2019


Article type: Perspective
DOI: 10.1039/C9DT03480C
Dalton Trans., 2019, Advance Article

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    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, Advance Article , DOI: 10.1039/C9DT03480C

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