Synthesis and evaluation of new nifurtimox‐adamantane adducts with trypanocidal activity

What is it about?

The synthesis and pharmacological evaluation of the C-1 substituted adamantane hydrazones 1a-d, their C-2 substituted isomers 2a-d and the C-1 substituted adamantane furanoic carboxamides 3a-c is described. The new adamantane derivatives exhibited an interesting pharmacological profile, in terms of trypanocidal activity and selectivity. Of the compounds tested, the phenylacetoxy hydrazone 1b showed the most promising profile against African trypanosomes (IC50=11 ± 0.9 nM; SI=770).

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Why is it important?

The prime aim of this communique is to probe the minimum stereoelectronic requirements of these new adducts that are necessary for enhancing the trypanocidal action of nifurtimox and at the same time to lower its toxicity. The test results, being noteworthy, have intrigued us to pursue in the future further studies, by designing new derivatives bearing analogous structural features.