title: Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and evaluation of their antimalarial activity.
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 IC(50)-values of ≤25 μM.
authors.affiliation: Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
authors.forename: Matthias
authors.initials: M
authors.lastname: D'hooghe
authors.forename: Stéphanie
authors.initials: S
authors.lastname: Vandekerckhove
authors.forename: Karen
authors.initials: K
authors.lastname: Mollet
authors.forename: Karel
authors.initials: K
authors.lastname: Vervisch
authors.forename: Stijn
authors.initials: S
authors.lastname: Dekeukeleire
authors.forename: Liesbeth
authors.initials: L
authors.lastname: Lehoucq
authors.forename: Carmen
authors.initials: C
authors.lastname: Lategan
authors.forename: Peter J
authors.initials: PJ
authors.lastname: Smith
authors.forename: Kelly
authors.initials: K
authors.lastname: Chibale
authors.forename: Norbert
authors.initials: N
authors.lastname: De Kimpe