10.1021/jm9002632.s001 Matthias D’hooghe Matthias D’hooghe Stijn Dekeukeleire Stijn Dekeukeleire Karen Mollet Karen Mollet Carmen Lategan Carmen Lategan Peter J. Smith Peter J. Smith Kelly Chibale Kelly Chibale Norbert De Kimpe Norbert De Kimpe Synthesis of Novel 2-Alkoxy-3-amino-3-arylpropan-1-ols and 5-Alkoxy-4-aryl-1,3-oxazinanes with Antimalarial Activity American Chemical Society 2009 antimalarial activity Plasmodium falciparum Alkoxy micromolar potency Et 2O compound THF Antimalarial ActivityA variety show cytotoxicity IC 50 values 2009-07-09 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/Synthesis_of_Novel_2_Alkoxy_3_amino_3_arylpropan_1_ols_and_5_Alkoxy_4_aryl_1_3_oxazinanes_with_Antimalarial_Activity/2844379 A variety of novel <i>syn</i>-2-alkoxy-3-amino-3-arylpropan-1-ols was prepared through LiAlH<sub>4</sub>-promoted reductive ring-opening of <i>cis</i>-3-alkoxy-4-aryl-β-lactams in Et<sub>2</sub>O. The latter γ-aminoalcohols were easily converted into <i>cis</i>-5-alkoxy-4-aryl-1,3-oxazinanes using formaldehyde in THF. Both series of compounds were evaluated against a chloroquine sensitive strain of <i>Plasmodium falciparum</i> (D10), revealing micromolar potency for almost all representatives. Eleven compounds exhibited antimalarial activity with IC<sub>50</sub> values of ≤30 μM, and the majority of these compounds did not show cytotoxicity at the concentrations tested.