SYNTHESIS OF CHALCONE AND FLAVONE FROM VERATRALDEHYDE AND 2�-HYDROXYACETOPHENONE AND THE ACTIVITY ASSAY AS AN ANTIMALARIAL

ALVIA DHIA SHABRIAH, Drs. Bambang Purwono, M.Sc., Ph.D.

2017 | Skripsi | S1 KIMIA

Sintesis flavon telah dilakukan dari bahan dasar kalkon yang disintesis dari veratraldehida dan 2'-hidroksiasetofenon. Uji aktivitas antimalaria kedua senyawa hasil sintesis telah dilakukan secara in vitro dengan uji penghambatan polimerisasi hem (HPIA). Sintesis diawali melalui kondensasi Claisen-Schmidt dengan mereaksikan veratraldehida dan 2'-hidroksiasetofenon dalam pelarut metanol dengan adanya natrium hidroksida yang direfluks selama 4 jam menghasilkan 2'-hidroksi-3,4-dimetoksikalkon. Selanjutnya, senyawa kalkon dilakukan proses siklisasi oksidatif menggunakan iodin dalam DMSO dan direfluks selama satu jam menghasilkan 3',4'-dimetoksiflavon. Kedua produk kemudian dianalisis menggunakan GC-MS, 1H-, and 13C-NMR spectrometer. Uji aktivitas antimalaria dilakukan secara in vitro dengan uji penghambatan polimerisasi hem untuk senyawa kalkon dan flavon. Senyawa kalkon yang diperoleh berupa padatan kuning terang dengan rendemen 40.53% dan titik leleh 104-107 C. Senyawa flavon yang diperoleh berupa padatan kuning dengan rendemen 49.65% dan titik leleh 144-147 C. Uji penghambatan polimerisasi hem menghasilkan nilai IC50 senyawa kalkon yaitu 0.146 mM dan senyawa flavon yaitu 0.007 mM. Nilai tersebut dapat disimpulkan bahwa kedua senyawa tersebut aktif sebagai aktivitas penghambatan polimerisasi hem.

Synthesis of flavone has been carried out from a based material of chalcone that synthesized from veratraldehyde and 2'-hydroxyacetophenone. Antimalarial activity assay of those synthesized compounds has been conducted in vitro by heme polymerization inhibitory assay (HPIA). The synthesis started with Claisen-Schmidt condensation by reacting veratraldehyde and 2'-hydroxyacetophenone in methanol solvent with the presence of sodium hydroxide under reflux for 4 h to give 2'-hydroxy-3,4-dimetoxychalcone. Furthermore, the treatment of chalcone by oxidative cyclization process using iodine in DMSO refluxed for 1 h gave 3',4'-dimethoxyflavone. Both of the products were analyzed by FTIR, GC-MS, 1H-, and 13C-NMR spectrometers. Antimalarial activity assay was conducted in vitro by heme polymerization inhibitory assay for chalcone and flavone compounds. The chalcone was obtained as bright yellow solid in 40.53% yield with melting point of 104-107 C. The flavone was obtained as yellow solid in 49.65% yield with melting point of 144-147 C. The heme polymerization inhibitory assay produced IC50 values of chalcone at 0.146 mM and flavone at 0.007 mM. These values implied that both of those compounds were active as heme polymerization inhibitory activity.

Kata Kunci : Flavone, chalcone, antimalarial, veratraldehyde, hematin, HPIA