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Muhammad Idham Darussalam Mardjan
Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281
Chemical Engineering, Chemistry & Bioengineering Chemistry

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Synthesis and Heme Polymerization Inhibitory Activity (HPIA) Assay of Antiplasmodium of (1)-N-(3,4-Dimethoxybenzyl)-1,10-Phenanthrolinium Bromide from Vanillin Dhina Fitriastuti; Muhammad Idham Darussalam Mardjan; Jumina Jumina; Mustofa Mustofa
Indonesian Journal of Chemistry Vol 14, No 1 (2014)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (263.489 KB) | DOI: 10.22146/ijc.21260

Abstract

The synthesis of (1)-N-(3,4-dimethoxy-benzyl)-1,10-phenanthrolinium bromide had been conducted from vanillin. Heme polymerization inhibitory activity assay of the synthesized antiplasmodium has also been carried out. The first step of reaction was methylation of vanillin using dimethylsulfate and NaOH. The mixture was refluxed for 2 h to yield veratraldehyde in the form of light yellow solid (79% yield). Methylation product was reduced using sodium borohydride (NaBH4) with grinding method and yielded veratryl alcohol in the form of yellow liquid (98% yield). Veratryl alcohol was brominated using PBr3 to yield yellowish black liquid (85% yield). The final step was benzylation of 1,10-phenanthroline monohydrate with the synthesized veratryl bromide under reflux condition in acetone for 14 h to afford (1)-N-(3,4-dimethoxy-benzyl)-1,10-phenanthrolinium bromide (84%) as yellow solid with melting point of 166-177 °C. The structures of products were characterized by FT-IR, GC-MS and 1H-NMR spectrometers. The results of heme polymerization inhibitory activity assay of (1)-N-(3,4-dimethoxybenzyl)-1,10-phenanthrolinium bromide showed that it had IC50 HPIA of 3.63 mM, while chloroquine had IC50 of4.37 mM. These results indicated that (1)-N-(3,4-dimethoxybenzyl)-1,10-phenanthrolinium bromide was more potential antiplasmodium than chloroquine.
SYNTHESIS OF FLAVANONE-6-CARBOXYLIC ACID DERIVATIVES FROM SALICYLIC ACID DERIVATIVE Muhammad Idham Darussalam Mardjan; Retno Ambarwati; Sabirin Matsjeh; Tutik Dwi Wahyuningsih; Winarto Haryadi
Indonesian Journal of Chemistry Vol 12, No 1 (2012)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (339.57 KB) | DOI: 10.22146/ijc.21374

Abstract

Synthesis of flavanone-6-carboxylic acid derivatives had been conducted via the route of chalcone. The synthesis was carried out from salicylic acid derivative, i.e. 4-hydroxybenzoic acid, via esterification, Fries rearrangement, Claisen-Schmidt condensation and 1,4-nucleophilic addition reactions. Structure elucidation of products was performed using FT-IR, 1H-NMR, GC-MS and UV-Vis spectrometers. Reaction of 4-hydroxybenzoic acid with methanol catalyzed with sulfuric acid produced methyl 4-hydroxybenzoate in 87% yield. The acid-catalyzed-acetylation of the product using acetic anhydride gave methyl 4-acetoxybenzoate in 75% yield. Furthermore, solvent-free Fries rearrangement of methyl 4-acetoxybenzoate in the presence of AlCl3 produced 3-acetyl-4-hydroxybenzoic acid as the acetophenone derivatives in 67% yield. Then, Claisen-Schmidt condensation of the acetophenone and benzaldehyde derivatives of p-anisaldehyde and veratraldehyde in basic condition gave 2'-hydroxychalcone-5'-carboxylic acid derivatives  in 81 and 71 % yield, respectively. Finally, the ring closure reaction of the chalcone yielded the corresponding flavanone-6-carboxylic acids in 67 and 59% yield, respectively.
Co-Authors Dhina Fitriastuti Jumina Jumina Mustofa Mustofa Retno Ambarwati Sabirin Matsjeh Tutik Dwi Wahyuningsih Winarto Haryadi