Diaxial diureido decalins as compact, efficient, and tunable anion transporters

S. Hussain, P. R. Brotherhood, L. W. Judd, A. P. Davis*

J. Am. Chem. Soc. 2011, 133, 1614–1617


Decalins bearing two axial −NHCONHAr substituents and an ester-linked alkyl side chain have been synthesized and studied as anion receptors and transporters. The design relates to steroid-based “cholapods” but is more compact and less intrinsically lipophilic. Transport rates depend on both NHAr and the alkyl side chain. High activities can be achieved; with optimal substitution, chloride-nitrate exchange across vesicle membranes is measurable at transporter/lipid ratios as low as 1:250 000.