SYNTHESIS ANTIBACTERIA COMPOUND VIA CINCHONA ALKALOIDS TRANSFORMATION

• Main Author: Aria Kamandanu, Sendi
• Format: Final Project
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/38080
• Institution: Institut Teknologi Bandung

Cinchona plants has been well known as a source of alkaloids for antimalaria drugs. Indonesia produce annually Cinchona alkaloids 150 tons. However, the use of Cinchona alkaloids as first line of antimalaria agent has been replaced by other drugs such as chloroquine and artemisinin. Besides its important bioactivity, Cinchona alkaloid can also be applied as chiral pool in synthesis asymmetric. In this research, cinchonine, one of the major component in Cinchona alkaloids, was used as building block in drug synthesis. The aims of this study were to diversify Cinchona alkaloids derivatives as an contribution to utilize Cinchona source in Indonesia. Cinchonine have been successfully converted to a new class of antibacterial agent namely quinolylpropylpiperidine which is active against Psedomonas sp., a microbe caused nosocomial infection. Hoffmann elimination of cinchonine in the present of acetic acid glacial yielded enol group which converted spontaneously to ketone to produce cinchotoxine. The carbonyl group of cinchotoxine was identified in 13C-NMR by the chemical shift at 202.9 ppm. Furthermore, the secondary amine of cinchotoxine was indicated in 1H-NMR by chemical shift at 2.32 ppm. Interconvertion of ketone group to oxime group carried out by using hydroxylamine as reagent under basic condition. The oxime cinchotoxide was charactherized by 13C-NMR by the chemical shift at 153.4 ppm.This synthetic method can be applied as a general method for the synthesis of quinolylpropylpiperidine type of antibacterial agent from Cinchona alkaloids.