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All Journal Indonesian Journal of Chemistry Makara Journal of Science Molekul: Jurnal Ilmiah Kimia
Muhammad Idham Darussalam Mardjan
Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281
Biochemistry, Genetics & Molecular Biology Chemical Engineering, Chemistry & Bioengineering Chemistry Materials Science & Nanotechnology

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Synthesis of 1-(4-Ethoxy-3-methoxybenzyl)-1,10-phenanthrolin-1-ium Bromide and Its Evaluation as Antiplasmodium through Heme Polymerization Inhibitory Activity (HPIA) Assay Fitriastuti, Dhina; Alfiyah, Viny; Mustofa, Mustofa; Jumina, Jumina; Mardjan, Muhammad Idham Darussalam
Makara Journal of Science Vol. 25, No. 1
Publisher : UI Scholars Hub

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Abstract

This study describes the development of N-benzyl-1,10-phenantrolinium salt as an antiplasmodium agent. The salt, that is, 1-(4-ethoxy-3-methoxybenzyl)-1,10-phenanthrolin-1-ium bromide, was prepared using vanillin as the starting material in four simple synthetic steps. First, the alkylation of vanillin using diethyl sulfate produced 4-ethoxy-3-methoxybenzaldehyde in 79% yield. Second, the reduction of the protected vanillin by NaBH4 through the grinding method allowed us to obtain 4-ethoxy-3-methoxybenzyl alcohol in 96% yield. Next, the bromination of the benzyl alcohol under solvent-free condition led to the formation of the corresponding benzyl bromide, which in turn underwent bimolecular nucleophilic substitution with 1,10-phenanthroline to produce the desired product, that is, 1-(4-ethoxy-3-methoxybenzyl)-1,10-phenanthrolin-1-ium bromide, in 58% yield. The evaluation of N-benzyl-1,10-phenantrolinium salt as an antiplasmodium agent was conducted through heme polymerization inhibitory activity (HPIA) assay. The results showed that the phenantroline salt and chloroquine displayed the HPIA half maximal inhibitory concentrations of 3.63 and 4.37 mM, respectively. Therefore, 1-(4-ethoxy-3-methoxybenzyl)-1,10-phenanthrolin-1-ium bromide displays desirable HPIA and has a great potential to be further developed as an antiplasmodium.
Synthesis, Activity Test and Molecular Docking of Novel Nitrophenylcalix[4]-2-methylresorcinarene Derivatives as Antimalarial Agent Nisa, Siti Astika; Jumina, Jumina; Mardjan, Muhammad Idham Darussalam; Kurniawan, Yehezkiel Steven
Molekul Vol 18 No 3 (2023)
Publisher : Universitas Jenderal Soedirman

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20884/1.jm.2023.18.3.7866

Abstract

This research involved the synthesis, antimalarial assay and molecular docking of novel nitrophenylcalix[4]-2-methylresorcinarene derivatives. Calix[4]-2-methylresorcinarene derivatives, i.e., 2N, 3N and 4N, were synthesized in a one-step reaction through the cyclo-condensation reaction between resorcinol and aldehydes, i.e., 2-nitrobenzaldehyde, 3-nitrobenzaldehyde and 4-nitrobenzaldehyde, respectively. The reaction was carried out through the reflux method with ethanol and hydrochloric acid 37% as the solvent and catalyst, respectively. The synthetic products were characterized using FTIR, 1H-NMR, 13C-NMR, and LC-MS spectrometers. Furthermore, the in vitro antimalarial assay was carried out against Plasmodium falciparum strain 3D7. The results showed that the 2N, 3N and 4N compounds were successfully synthesized in 86.4, 78.6 dan 95.7% yield, respectively. The antimalarial activity test of 2N, 3N and 4N gave IC50 values of 2.35, 1.68 and 1.79 µM, therefore, these compounds are classified as active antimalarial agents. Molecular docking performed against the PfLDH receptor showed that the 2N, 3N and 4N compounds had negative binding affinity values of -5.1, -6.1, and -6.0 kcal/mol and had specific interactions in the form of hydrogen bonds to the amino acid residues Arg109, Thr101 and Lys102 in the active site of the receptor. The molecular docking results agreed with the experimental antimalarial assay demonstrating the mechanism of action of nitrophenylcalix[4]-2-methylresorcinarenes as active antimalarial agents happened through the inhibition of the PfLDH receptor.
Molecular Docking, Synthesis and In Vitro Antiplasmodium Assay of Monoketone Curcumin Analogous from 2-Chlorobenzaldehyde Mustika, Chessy Rima; Astuti, Endang; Mardjan, Muhammad Idham Darussalam
Indonesian Journal of Chemistry Vol 24, No 3 (2024)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.22146/ijc.81122

Abstract

This research aimed to develop new curcumin analogous as antiplasmodium candidates. Six curcumin analogous (1-6) were proposed and docked against three Plasmodium falciparum receptors, namely PfENR, PfLDH, and PfATP6. The docking studies were carried out to predict the interaction among the compounds and receptors as well as their binding affinity. Three curcumin analogous (3, 4, and 6), which displayed specific interactions with the target receptors and possessed the lowest binding affinity were further proceeded to synthesis and in vitro antiplasmodium assay. Synthesis of the analogous 3, 4, and 6 was carried out from 2-chlorobenzadehyde via aldol condensation reaction and the products were obtained in good yields. Their in vitro antiplasmodium activities were then evaluated against P. falciparum FCR3 and 3D7 strains. The results showed that analogous 3, 4, and 6 were active against both strains with low levels of resistance. The in silico evaluation of the physicochemical and pharmacokinetic parameters showed that curcumin analogous displayed a better ADMET profile than curcumin, demonstrating the great potential of the developed curcumin analogous as antiplasmodium candidates.
Synthesis, in Vitro Studies of Monocarbonyl Curcumin Analog Compounds Against Breast Cancer Cells and Normal Vero Cells, and In Silico Studies on Protein Variation Astuti, Endang; Rahmawati, Widya; Sulistya, Rahmawati; Chabib, Ircham Nur; Wahyuningsih, Tutik Dwi; Raharjo, Tri Joko; Mardjan, Muhammad Idham Darussalam
Molekul Vol 21 No 1 (2026)
Publisher : Universitas Jenderal Soedirman

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20884/1.jm.2026.21.1.13888

Abstract

ABSTRACT. The research aims to synthesize monocarbonyl analogs of curcumin (MAC) and evaluate their anticancer activity. The synthesis was carried out by sonication method through Claisen-Schmidt condensation reaction using base catalysts, namely potassium hydroxide and sodium hydroxide. Characterization of the compounds was carried out using TLC Scanner, ATR-IR, 1H-NMR, and 13C-NMR. Monocarbonyl analog of curcumin compounds A, B, and C have been successfully synthesized with purity of 91.13; 95.82; and 87.57%, respectively. The resulting compounds are yellow solids and have good yields. The monocarbonyl analog of curcumin compounds were then tested for cytotoxicity against breast cancer cells (T47D, MCF-7, and 4T1) and normal cells (Vero). Pharmacokinetic prediction and toxicity (ADMET) was performed using an online site (pkCSM). Monocarbonyl analogs of curcumin compounds were predicted to have a better pharmacokinetic profile compared to curcumin. Molecular docking was carried out using Autodock Vina to determine the interaction of curcumin and monocarbonyl curcumin analog compounds with EGFR, Bcl-2, and p53 mutants. Based on molecular docking, the proposed monocarbonyl analogs of curcumin generally exhibit lower binding affinities that curcumin and form specific interactions with amino acid residues inf target proteins. Keywords: Claisen-Schmidt condensation, molecular docking, monocarbonyl analog of curcumin.
Co-Authors Alfiyah, Viny Chabib, Ircham Nur Dhina Fitriastuti Endang Astuti Jumina Jumina Kurniawan, Yehezkiel Steven Mustika, Chessy Rima Mustofa Mustofa Nisa, Siti Astika Sulistya, Rahmawati Tri Joko Raharjo Tutik Dwi Wahyuningsih Widya Rahmawati