Synthesis of Novel Diazabicycles and their Antiprotozoal Activities

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Contents Vol 62(9)

doi:10.1071/CH09197

Synthesis of Novel Diazabicycles and their Antiprotozoal Activities

Volker Wolkinger ^A, Robert Weis ^A, Ferdinand Belaj ^B, Marcel Kaiser ^C, Reto Brun ^C, Robert Saf ^D, Werner Seebacher ^A ^E

^A Institute of Pharmaceutical Sciences, Pharmaceutical Chemistry, Karl-Franzens-University, Universitätsplatz 1, A-8010 Graz, Austria.
^B Institute of Chemistry, Karl-Franzens-University Graz, Heinrichstrasse 28/IV, A-8010 Graz, Austria.
^C Swiss Tropical Institute, Socinstrasse 57, CH-4002 Basel, Switzerland.
^D Institute of Chemical Technology of Organic Materials, Erzherzog-Johann University, Stremayrgasse 26/1, A-8010 Graz, Austria.
^E Corresponding author. Email: we.seebacher@uni-graz.at





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Australian Journal of Chemistry 62(9) 1166–1172 http://dx.doi.org/10.1071/CH09197
Submitted: 7 April 2009 Accepted: 9 June 2009 Published online: 17 September 2009

Abstract

We describe the synthesis of new diaryl substituted diazabicyclo[3.2.1]octanes from diazepanes which were prepared by the reduction of diazepanones. The formation of the bicyclic system was optimized by microwave irradiation and the structures of the new compounds were established by single crystal structure analysis and NMR spectroscopy. All new compounds were tested for their potencies against Plasmodium falciparum K₁ and Trypanosoma b. rhodesiense, the causative organisms of malaria tropica and the East African form of sleeping sickness.