Virtual ligand screening of a publicly available database of antimalarial hits using a pharmacophore derived from antimalarial MMV008138 identified TCMDC-140230, a tetrahydro-β-carboline amide, as worthy of exploration. All four stereoisomers of this structure were synthesized, but none potently inhibited growth of the malaria parasite <i>Plasmodium falciparum</i>. Interestingly, <b>7e</b>, a minor byproduct of these syntheses, proved to be potent <i>in vitro</i> against <i>P. falciparum</i> and was orally efficacious (40 mg/kg) in an <i>in vivo</i> mouse model of malaria.