One-Pot Synthesis and In Vitro Studies of Calix[4]-2-methylresorcinarene Derivatives as Antimalarial Agents Against Plasmodium falciparum Chloroquine-Resistant Strain FCR-3

Nursofia, Baiq Ike and Kurniawan, Yehezkiel Steven and Jumina, Jumina and Pranowo, Harno Dwi and Sholikhah, Eti Nurwening and Julianus, Jeffry and Wibowo, Susalit Setya and Fatimi, Hana Anisa and Priastomo, Yoga and Priyangga, Krisfian Tata Aneka (2024) One-Pot Synthesis and In Vitro Studies of Calix[4]-2-methylresorcinarene Derivatives as Antimalarial Agents Against Plasmodium falciparum Chloroquine-Resistant Strain FCR-3. Indonesian Journal of Chemistry, 24 (6). p. 1717. ISSN 14119420

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Abstract

Malaria is an endemic disease in Indonesia caused by infection from the Plasmodium parasite. Recently, antimalarial resistance significantly contributed to the decline in the cure rate of malaria sufferers. In this work, three calix[4]resorcinarenes have been synthesized from 2-methylresorcinol and different benzaldehyde derivatives, i.e., 4-chlorobenzaldehyde, 4-methoxybenzaldehyde, and 4-dimethylaminobenzaldehyde through the one-pot synthesis procedure. The calix[4]resorcinarenes synthesis was done through a cyclo-condensation reaction by using HCl 37% as the catalyst and ethanol as the solvent in an one-pot reaction. The structures of the synthesized products were confirmed using Fourier transform infrared, proton-nuclear magnetic resonance, and liquid chromatography-mass spectrometry techniques. The antimalarial activity assay was evaluated against the Plasmodium falciparum FCR-3 strain through an in vitro study. Three synthesized compounds, i.e., C-4-chlorophenylcalix[4]-2-methylresorcinarene, C-4-methoxyphenylcalix[4]-2-methylresorcinarene and C-4-dimethylaminophenylcalix[4]-2-methylresorcinarene have been successfully synthesized in up to 97% yield. The C-4-chlorophenylcalix[4]-2-methylresorcinerene exhibited the most potent antimalarial activity with a half-maximal inhibitory concentration (IC50) value of 2.66 μM against P. falciparum FCR-3 while the C-4-methoxyphenylcalix[4]-2-methylresorcinarene and C-4-dimethylaminophenylcalix[4]-2-methylresorcinarene gave the IC50 values of 23.63 and 13.82 μM, respectively. From the results, it could be concluded that the antimalarial activity of calix[4]-2-methylresorcinarenes was influenced by the type of substituent of aromatic rings at the para position.

Item Type: Article
Uncontrolled Keywords: Antimalarial; calix[4]-2-methylresorcinarene; in vitro assay; one-pot synthesis; Plasmodium falciparum
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Mathematics and Natural Sciences > Chemistry Department
Depositing User: Wiyarsih Wiyarsih
Date Deposited: 13 Mar 2025 07:08
Last Modified: 13 Mar 2025 07:08
URI: https://ir.lib.ugm.ac.id/id/eprint/15741

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