Design, synthesis, and trypanocidal activity of new aminoadamantane derivatives

Papanastasiou, I; Tsotinis, A; Kolocouris, N; Prathalingam, SR; Kelly, JM; (2008) Design, synthesis, and trypanocidal activity of new aminoadamantane derivatives. Journal of medicinal chemistry, 51 (5). pp. 1496-1500. ISSN 0022-2623 DOI:

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To develop functionalized adamantanes for treating African trypanosomiasis, we report on the synthesis of new 1-alkyl-2-aminoadamantanes 1a-i, 1-alkyltricyclo[,7)]decan-2-guanylhydrazones 2a-g, and their congeneric thiosemicarbazones 3a,b. The potency of these compounds against Trypanosoma brucei was compared to that of amantadine and rimantadine and found to be substantially higher. The most active analogues, 1c, 1d, 2c, 2g, and 3b, illustrate the synergistic effect of the lipophilic character of the C1 side chain and the C2 functionality on trypanocidal activity.

Item Type: Article
Faculty and Department: Faculty of Infectious and Tropical Diseases > Dept of Pathogen Molecular Biology
PubMed ID: 18281929
Web of Science ID: 253784900047


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