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  • Title: Synthesis of bicyclic amines and their activities against Trypanosoma brucei rhodesiense and Plasmodium falciparum K1.
    Author: Weis R, Berger H, Kaiser M, Brun R, Saf R, Seebacher W.
    Journal: Arch Pharm Res; 2008 Jun; 31(6):688-97. PubMed ID: 18563349.
    Abstract:
    New alkenes, aziridines, and diamines were prepared from antiprotozoal 4-dialkylaminobicyclo[2.2.2]octan-2-imines to investigate the influence of several functional groups in position 2 of the ring skeleton on the antitrypanosomal and antiplasmodial activities. They were synthesized from 4-dialkylaminobicyclo[2.2.2]octan-2-imines and tested for their activities against Trypanosoma b. rhodesiense and Plasmodium falciparum K1 (resistant to chloroquine and pyrimethamine) using in vitro microplate assays. 4-Aminobicyclo[2.2.2]oct-2-enes and 3-azatricyclo[3.2.2.0(2,4)]nonylamines exhibit similar antiprotozoal activities as 4-aminobicyclo[2.2.2] octanes. 4-Aminobicyclo[2.2.2]oct-2-ylamines and their N-benzyl derivatives showed decreased antiplasmodial but enhanced antitrypanosomal (IC50 = 0.22-0.41 microM) activities compared to their parent oximes and to formerly synthesized 4-amino-2-azabicyclo[3.2.2]nonanes. Some of the 4-aminobicyclo[2.2.2]oct-2-ylamines exhibit moderate in vivo activity in mice against Trypanosoma brucei brucei.
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