engleski

Adamantane compounds with a guanidine subunit : synthesis, characterization and application

Adamantane, a polycyclic cage molecule, possesses some unique properties, the most important being a pronounced lipophylicity. This is why some pharmacophores have an adamantyl fragment incorporated in their structure. On the other hand, compounds with a guanidine subunit are often promising drug candidates, mainly because of their high basicity and the ability to form strong hydrogen bonds. A combination of these two structural moieties in one molecule was hypothesized to bring about a synergy of chemical and physical properties. The main objective was to synthesize and fully characterize novel aminoguanidine derivatives containing the adamantane skeleton as a framework. These compounds were then tested as butyrylcholinesterase (BChE) inhibitors. In addition to the enzymatic bioactivity studies, the protonation and subsequent fragmentation of these compounds in the gas phase was also studied using the ESI-MS/MS technique. Mass spectrometry was used to gain additional insight into the intramolecular interactions of these compounds.

Aminoguanidine ; Adamantane ; Butyrylcholinesterase (BChE)

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