Synthesis of diphenoxyadamantane alkylamines with pharmacological interest

What is it about?

In this work, the synthesis and the pharmacological evaluation of diphenoxyadamantane alkylamines Ia-f and IIa-f is described. The new diphenoxy-substituted adamantanes share structural features present in trypanocidal and antitubercular agents. 1-Methylpiperazine derivative Ia is the most potent against T. brucei compound, whilst its hexylamine congener IIf exhibits a significant antimycobacterial activity.

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Why is it important?

The new adamantane derivatives presented herein are doubly substituted by a phenoxyl, incorporating various aminoalkyl side chains. The 1-methylpiperazine derivative Ia is the most active against T. brucei, while hexylamine IIf exhibits the higher antimycobacterial potency among its analogs. The ethylene spacer of the side chain leads to enhanced activity compared to the 2-hydroxypropylene linker. These preliminary results will be utilized in future studies on phenyl-substituted adamantane derivatives with a trypanocidal and antitubercular potency devoid of toxicity against mammalian cells.