Monatshefte für Chemie - Chemical Monthly

, Volume 150, Issue 11, pp 1959–1972 | Cite as

New derivatives of 3-azabicyclo[3.2.2]nonanes and their antiprotozoal activities

  • Michael Hoffelner
  • Markus Petritsch
  • Sarfraz Ahmad
  • Werner SeebacherEmail author
  • Johanna Dolensky
  • Patrick Hochegger
  • Marcel Kaiser
  • Pascal Mäser
  • Robert Saf
  • Robert Weis
Original Paper


New derivatives of 3-azabicyclo[3.2.2]nonanes were prepared and characterized using FT-IR spectroscopy, HRMS, and NMR spectroscopy. The new compounds were investigated in vitro for their antiplasmodial activities against the sensitive NF54 strain and the multiresistant K1 strain of Plasmodium falciparum, and for their antitrypanosomal activity against Trypanosoma brucei rhodesiense. The N-methyl-6,9-diphenyl-N-[(pyridin-4-yl)methyl]-3-azabicyclo[3.2.2]nonan-1-amine possessed high antiplasmodial in vitro activity against both strains of P. falciparum (NF54: IC50 = 0.848 nm; K1: IC50 = 2 nm). The most promising ones were further investigated in a mouse model for their in vivo activity against Plasmodium berghei.

Graphic abstract


Amines Antiplasmodial activity Antitrypanosomal activity Drug research Hybrids Structure–activity relationships 


Compliance with ethical standards

Ethical approval

In vivo efficacy studies in mice were conducted at the Swiss Tropical and Public Health Institute (Basel) according to the rules and regulations for the protection of animal rights (“Tierschutzverordnung”) of the Swiss “Bundesamt für Veterinärwesen”. They were approved by the veterinary office of Canton Basel-Stadt, Switzerland.


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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2019

Authors and Affiliations

  • Michael Hoffelner
    • 1
  • Markus Petritsch
    • 1
  • Sarfraz Ahmad
    • 2
  • Werner Seebacher
    • 1
    Email author
  • Johanna Dolensky
    • 1
  • Patrick Hochegger
    • 1
  • Marcel Kaiser
    • 3
  • Pascal Mäser
    • 3
  • Robert Saf
    • 4
  • Robert Weis
    • 1
  1. 1.Institute of Pharmaceutical SciencesUniversity of GrazGrazAustria
  2. 2.Department of Chemistry, Faculty of ScienceUniversity of MalayaKuala LumpurMalaysia
  3. 3.Swiss Tropical and Public Health Institute and University of BaselBaselSwitzerland
  4. 4.Institute for Chemistry and Technology of Materials (ICTM)Graz University of TechnologyGrazAustria

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