Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and evaluation of their antimalarial activity

• Matthias D’hooghe,
• Stéphanie Vandekerckhove,
• Karen Mollet,
• Karel Vervisch,
• Stijn Dekeukeleire,
• Liesbeth Lehoucq,
• Carmen Lategan,
• Peter J. Smith,
• Kelly Chibale and
• Norbert De Kimpe

Beilstein J. Org. Chem. 2011, 7, 1745–1752, doi:10.3762/bjoc.7.205

• antiplasmodial activity against both a chloroquine-sensitive and a chloroquine-resistant strain of Plasmodium falciparum with IC50-values of ≤25 μM. Keywords: aminopropanes; antimalarial activity; aziridines; β-lactams; ring opening; Introduction Malaria remains a major issue in health control, especially in

• )aziridines by diethylamine [8]. Nonetheless, a number of challenges with regard to structure–activity relationship studies of functionalized aminopropanes remain unaddressed, especially concerning the screening of structural analogues of aminopropanes 1 and 2. In the present paper, the synthesis of racemic

• approach is disclosed towards racemic aminopropanes 4 bearing a 1,2,3-triazole moiety, as structural analogues of the previously reported 1,2,4-triazoles 2 (Figure 1). Both classes of functionalized aminopropanes 3 and 4 were tested for their antiplasmodial activity. Results and Discussion Synthesis Within