Adamantyl aminoguanidines as receptors for oxo-anions

Adamantane in Drug Delivery Systems and Surface Recognition

“…As the molecules were encapsulated into multilamellar liposomes, the guanidine subunit remained on the outer side of the bilayer pointing outward and thus was enabling the formed vesicle to engage in surface recognition. Supramolecular binding mediated with these guanidine sites is feasible since it is known from the literature that guanidine forms parallel hydrogen bonds with oxoanions [ 48 ] and the same is true for the studied adamantyl aminoguanidines [ 49 ].…”

A Multidisciplinary Approach to the Study of Adamantyl Aminoguanidines – A New Class of Potentially Bioactive Compounds

“…3 This further encouraged us to undertake a systematic study of this type of compounds, covering various aspects of their nature and properties. [4][5][6][7][8] The most facile way to synthesize adamantyl guanylhydrazones was to use the corresponding adamantyl ketones as a key starting material. On the other hand, in order to prepare adamantyl aminoguanidines we used the corresponding adamantyl amines (Scheme 1).…”

“…The studies we conducted included a structural characterization of all the possible compound geometries using a computational approach, [4][5][6] fragmentation studies in the gas phase, 4 oxo-anion binding studies, 7 enzyme-inhibition testing, 8 and their incorporation into the liposomes. 5 We calculated the enthalpies for compounds 1-12 and for all of their isomers using B3LYP/6-311+G (d,p) level of theory.…”

“…Although numerous artificial guanidine receptors are known in the literature, 13 to the best of our knowledge, no research has been done on aminoguanidine derivatives prior to our recent study. 7 The main advantage of aminoguanidine over guanidine in a potential receptor is the presence of the additional amino group that can serve as another H-bond donor which can take part in the binding interactions. We tested adamantyl aminoguanidines 7-10 as anion receptors by means of 1 H NMR titration experiments in a DMSO-d 6 solution using the TBA salts of selected oxoanions (AcO -, HSO 4 -, and H 2 PO 4 -).…”

Synthesis and Anion Binding Assessment of Novel Adamantane Amidopyrroles

“…Our research group investigated synthesis and anion binding properties of pyrrole, [20] urea [21] and guanidine [22] receptors that contained adamantane as a polycyclic unit in the structure. We hypothesized that incorporation of a rigid and bulky adamantane moiety between the symmetrical binding sites would diminish rotational mobility of the sensor and in that way somewhat preorganize it for anion trapping.…”