Novel Adamantane-Bearing Anilines and Properties of Their Supramolecular Complexes with beta-Cyclodextrin

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Authors	VÍCHA Robert ROUCHAL Michal KOZUBKOVÁ Zuzana KUŘITKA Ivo MAREK Radek BRANNÁ Petra ČMELÍK Richard
Year of publication	2011
Type	Article in Periodical
Magazine / Source	Supramolecular Chemistry
MU Faculty or unit	Faculty of Science
Citation
Web	DOI: 10.1080/10610278.2011.593628
Doi	http://dx.doi.org/10.1080/10610278.2011.593628
Field	Organic chemistry
Keywords	Adamantane; Amines; Cyclodextrins; Host-guest systems
Attached files	SupraCh11_23_663.pdf
Description	Several novel anilines bearing 1-adamantyl substituents that are useful for drug modification were synthesised from the corresponding 1-adamantyl (nitrophenyl) ketones. The host-guest systems of these prepared ligands with beta-cyclodextrin were studied using ESI-MS, NMR spectroscopy, titration calorimetry, and semi-empirical calculations. The complexes with 1:1 stoichiometry were found to predominantly exist as pseudorotaxane threaded structures with the adamantane cage sitting in the wider rim of beta-cyclodextrin. Such geometry was observed for all examined amines and is independent of their structure and/or presence of protic substituents.
Related projects:	Proteins in metabolism and interaction of organisms with the environment