Synthesis of aryl amino alcohol derivate from turpentine oil as a potential antimalarial drug

Abstract

The parasite of Plasmodium causes malaria disease, attacking the red blood cells of humans and survive by utilizing the nutrients from the breakdown of hemoglobin into free heme and globin. Free heme is toxic to the parasite so that it converts into hemozoin through heme polymerization. This research aims to synthesize aryl amino alcohol derivative from the reaction of epoxide compound from turpentine oil containing α-pinene with naphthylamine. The antimalarial activity of the compound was tested using heme polymerization inhibitory assay. Firstly, the epoxidation of α-pinene of turpentine oil was conducted using H2O2 as an oxidizing agent with Al2O3 as a catalyst. The mixture was filtrated then the filtrate was added by naphthylamine. The product was isolated using preparative thin layer chromatography method. Product identification was carried out by Thin Layer Chromatography (TLC), infrared (IR) spectrophotometer, proton nuclear magnetic resonance spectrometer (1H-NMR) and Electrospray Ionization-Mass Spectrometer (ESI-MS). This research was obtained a compound of 2,6,6-trimethyl-2-(naphthalen-1-ylamino) bicyclo[3.1.1]heptan-3-ol. The synthesized compound has a lower IC50 value (1.114 mg/mL) compared to chloroquine (1.31 mg/mL) so that it is potential as an antimalarial drug.