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

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

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

Journal Article

2011

Journal Title

Beilstein Journal of Organic Chemistry

Link to Journal

https://dx.doi.org/10.3762/bjoc.7.205

Department

Department of Chemistry

Faculty

Faculty of Science

Abstract

A variety of 2-amino-3-arylpropan-1-ols, anti-2-amino-3-aryl-3-methoxypropan-1-ols and anti-2-amino-1-arylpropan-1,3-diols were prepared selectively through elaboration of trans-4-aryl-3-chloro-β-lactams. In addition, a number of 2-(azidomethyl)aziridines was converted into novel 2-[(1,2,3-triazol-1-yl)methyl]aziridines by Cu(I)-catalyzed azide-alkyne cycloaddition, followed by microwave-assisted, regioselective ring opening by dialkylamine towards 1-(2,3-diaminopropyl)-1,2,3-triazoles. Although most of these compounds exhibited weak antiplasmodial activity, six representatives showed moderate antiplasmodial activity against both a chloroquine-sensitive and a chloroquine-resistant strain of Plasmodium falciparum with IC50-values of ≤25 μM.