ArticleAntimicrobial agents and chemotherapy2001
In vitro and in vivo activities of aminoadamantane and aminoalkylcyclohexane derivatives against Trypanosoma brucei.
Article in Antimicrobial agents and chemotherapy, 2001. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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9 citing papers in PubMed, 31 citations in OpenAlex.
- Synthesis and Evaluation of Nitroheterocyclic Aromatic Adamantanohydrazones with Trypanocidal Activity. Part III.ACS infectious diseases · 2026Article
- A Novel High-Content Phenotypic Screen To Identify Inhibitors of Mitochondrial DNA Maintenance in Trypanosomes.Antimicrobial agents and chemotherapy · 2022Article
- Antiprotozoal Activity Profiling of Approved Drugs: A Starting Point toward Drug Repositioning.PloS one · 2015Article
- The lipophilic bullet hits the targets: medicinal chemistry of adamantane derivatives.Chemical reviews · 2013Review
- Synthesis of benzopolycyclic cage amines: NMDA receptor antagonist, trypanocidal and antiviral activities.Bioorganic & medicinal chemistry · 2012Article
- Novel lipophilic acetohydroxamic acid derivatives based on conformationally constrained spiro carbocyclic 2,6-diketopiperazine scaffolds with potent trypanocidal activity.Journal of medicinal chemistry · 2011Article
- Synthesis and pharmacological evaluation of (2-oxaadamant-1-yl)amines.Bioorganic & medicinal chemistry · 2009Article
- Synthesis and pharmacological evaluation of several ring-contracted amantadine analogs.Bioorganic & medicinal chemistry · 2008Article
- Design, synthesis, and trypanocidal activity of new aminoadamantane derivatives.Journal of medicinal chemistry · 2008Article
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Authors and funding
3 authors at 2 institutions in 2 countries.
Funding
Abstract
We reported recently that the bloodstream form of the African trypanosome, Trypanosoma brucei, is sensitive to the anti-influenza virus drug rimantadine. In the present report we describe the trypanocidal properties of a further 62 aminoadamantane and aminoalkylcyclohexane derivatives. Seventeen of the compounds were found to be more active than rimantadine, with four inhibiting growth in vitro of T. brucei by >90% at concentrations of 1 microM. The most active derivative (1-adamantyl-4-amino-cyclohexane) was about 20 to 25 times more effective than rimantadine. We observed a correlation between structural features of the derivatives and their trypanocidal properties; hydrophobic substitutions to the adamantane or cyclohexane rings generally enhanced activity. As with rimantadine, the activity in vitro varied with the pH. T. brucei was more sensitive in an alkaline environment (including a normal bloodstream pH of 7.4) and less sensitive under acidic conditions. Tests for activity in vivo were carried out with a mouse model of infection with a virulent strain of T. brucei. Although the parasitemia was not eliminated, it could be transiently suppressed by >98% with the most active compounds tested. These results suggest that aminoadamantane derivatives could have potential as a new class of trypanocidal agents.
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