STUDY OF SYNTHESIS OF LICOCHALCONE A FOR ACT (ARTEMISININ COMBINATION THERAPY) COMPONENT ON MALARIA HANDLING

• Main Author: Maria Widyasari, Eva
• Format: Theses
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/35429
• Institution: Institut Teknologi Bandung

Chalcone is a secondary metabolites natural plant and precursors in the biosynthesis of flavonoid. Licochalcone A showed an antimalarial activity both in vitro and in vivo as well as combination with artemisinin as the ACT which have a synergistic activity against sensitive or resistant Plasmodium to chloroquine. The activity of ACT showed more active than artemisinin monotherapy. The action mechanism of licochalcone A as antimalarial is reported by inhibiting the cysteine protease which responsible for hemoglobin degradation process. The process produce an amino acid needed by Plasmodium. Retrosynthetic analysis showed that licochalcone A can be synthesized via C6-C2 + C1-C6 strategy. Reaction of acetophenone and benzaldehid in alkaline condition yield usually chalcone derivatives. This study has been successfully synthesized two main fragments are acetophenone and benzaldehide for synthesis of licochalcone A. 4-TBDMS acetophenone compound have been successfully synthesized by a two-step reaction consist of a regioselective acylation of phenol and protection of hydroxyl group by using TBDMS. The protection of the hydroxyl group will prevent the formation of side reactions on the formation chalcone. The compound 2-methoxy-4-O-prenil benzaldehide was synthesized via a three-steps reaction, carbonylation of resorcinol using Reimer-Tiemann reaction, followed by a regioselective prenylation of resorcylaldehyde product and methylation of o-hydroxy group with dimethylsulfate. All products were characterized using MS spectral data, UV-Vis, FTIR, and NMR.