Synthesis and Evaluation of Nifurtimox-Adamantane Adducts with Trypanocidal Activity.

Foscolos, Angeliki-Sofia; Papanastasiou, Ioannis; Tsotinis, Andrew; Taylor, Martin C; Kelly, John M; (2019) Synthesis and Evaluation of Nifurtimox-Adamantane Adducts with Trypanocidal Activity. ChemMedChem, 14 (13). pp. 1227-1231. ISSN 1860-7179 DOI: https://doi.org/10.1002/cmdc.201900165

Abstract

The synthesis and pharmacological evaluation of C1-substituted adamantane hydrazones, their C2-substituted isomers, and C1-substituted adamantane furanoic carboxamides is described. These new adamantane derivatives exhibited an interesting pharmacological profile in terms of trypanocidal activity and selectivity. The most active adduct with the best selectivity in this study was found to be the phenylacetoxy hydrazone 1 b (2-[4-(tricyclo[3.3.1.13,7 ]dec-1-yl)phenyl]-N'-[(5-nitrofuran-2-yl)methylene]acetohydrazide; EC50 =11±0.9 nm, SITb =770).