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.