engleski

SYNTHESIS OF NOVEL ADAMANTANE PYRROLECARBOXYAMIDES

Designing pyrrole-based anion receptors combined with various hydrogen bond donor groups (amino, amide, guanidine, etc.) is a continuing challenge in the field of supramolecular chemistry [1]. Our previous investigation in the field included adamantane-dipyrromethanes, receptors with acidic pyrrole NH proton and with additional hydrogen bond donor or electron withdrawing substituent [2]. Therefore, our next step is the combination of NH-amide groups and NH-pyrrole, thus designing receptors 1 and 2 that could bind anions in more competitive solvents. Additionally, we presume that the binding sites separated by various alkyl linkers (methyl or ethyl) on a rigid adamantane spacer would enable encapsulation of anions possessing different sizes and shapes, thus achieving anion selectivity. On the other hand, it is known that short pyrrole amides strongly bind to the minor groove of DNA, which was found to be a requirement for good antibacterial activity [3]. Furthermore, incorporation of a lipophilic unit surely can have an impact on biological activity and could facilitate potential antimicrobial application. Herein we report the synthesis of new adamantane pyrrolecarboxyamides 1 and 2 starting from pyrrole, and implementation of two different amide coupling reactions as key steps.

adamantane; pyrrolecarboxyamides; anion receptors

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