SINTESIS SENYAWA ANALOG KURKUMIN DARI VANILIN TERBROMINASI DAN UJI AKTIVITASNYA SEBAGAI ANTIMALARIA

RAFIAN AZHAR A R, Drs. Bambang Purwono, M.Sc, Ph.D

2018 | Skripsi | S1 KIMIA

Sintesis senyawa analog kurkumin (2,6-bis(5-bromo-4-hidroksi-3-metoksi benzilidin)sikloheksa-1-on) dari vanillin dan telah dilakukan uji aktivitasnya sebagai antimalaria. Senyawa 2,6-bis(5-bromo-4-hidroksi-3-metoksibenzilidin)sikloheksa-1-on disintesis melalui vanillin yang dibrominasi kemudian direaksikan dengan sikloheksanon. Senyawa 2,6-bis(4-hidroksi-3-metoksibenzilidin)sikloheksa-1-on disintesis dengan mereaksikan langsung antara vanillin dengan sikloheksanon. Senyawa hasil sintesis kemudian dianalisis dengan spektrofotometer FTIR, spektrometer MS, dan 1H-NMR. Analog kurkumin hasil sintesis kemudian diuji aktivitasnya sebagai antimalaria dengan metode penghambatan polimerisasi hem. Hasil sintesis senyawa 2,6-bis(4-hidroksi-3-metoksibenzilidin)sikloheksa-1-on menghasilkan rendemen sebanyak 83,79% dan hasil sintesis senyawa 2,6-bis(5-bromo-4-hidroksi-3-metoksibenzilidin)sikloheksa-1-on menghasilkan rendemen sebanyak 42,54%. Kedua senyawa analog kurkumin memiliki aktivitas antimalaria dengan IC50 19,95 mM dan 20,88 mM, sedangkan IC50 klorokuin sebagai kontrol positif 6,03 mM.

Synthesis of curcumin analogue (2,6-bis(5-bromo-4-hydroxy-3-methoxybenzylidene) cyclohexanone) from brominated vanillin and assays activities as antimalarial have been conducted. The compound of 2,6-bis(5-bromo-4-hydroxy-3-methoxy benzylidene)cyclohexanone synthesized through vanillin brominated was then reacted with cyclohexanone. The 2,6-bis(4-hydroxy-3-methoxybenzylidene) cyclohexanone was synthesized through reacting directly between vanillin with cyclohexanone. The synthesized compounds were then analyzed by FTIR spectrophotometer, MS spectrometer and 1H-NMR. The analogue curcumin were then tested the activities as antimalarial by hem polymerization inhibition method. The synthesis compound of 2,6-bis(4-hydroxy-3-methoxybenzylidene) cyclohexanone was produced 83.79% yield and the compound of 2,6-bis(5-bromo-4-hydroxy-3-methoxybenzylidene) cyclohexanone was produced 42.54% yield. Both compounds of curcumin analogue have antimalarial ativity with IC50 19.95 mM and 20.88 mM, meanwhile IC50 chloroquine as a positive control was 6.03 mM.

Kata Kunci : antimalaria, vanillin, bromovanilin, analog kurkumin.