Beilstein Journal of Organic Chemistry 2014-01-01

Synthesis of uniform cyclodextrin thioethers to transport hydrophobic drugs.

Lisa F Becker, Dennis H Schwarz, Gerhard Wenz

Index: Beilstein J. Org. Chem. 10 , 2920-2927, (2014)

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Abstract

Methyl and ethyl thioether groups were introduced at all primary positions of α-, β-, and γ-cyclodextrin by nucleophilic displacement reactions starting from the corresponding per-(6-deoxy-6-bromo)cyclodextrins. Further modification of all 2-OH positions by etherification with iodo terminated triethylene glycol monomethyl ether (and tetraethylene glycol monomethyl ether, respectively) furnished water-soluble hosts. Especially the β-cyclodextrin derivatives exhibit very high binding potentials towards the anaesthetic drugs sevoflurane and halothane. Since the resulting inclusion compounds are highly soluble in water at temperatures ≤37 °C they are good candidates for new aqueous dosage forms which would avoid inhalation anaesthesia.