Synthesis and Evaluation of Antiplasmodial Activity of 2,2,2-Trifluoroethoxychalcones and 2-Fluoroethoxy Chalcones against Plasmodium falciparum in Culture

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Kavita DeviManjula Singh

Abstract

A new class of compounds comprising two series of chalcones with 2,2,2-trifluoroethoxy group and 2-fluoroethoxy groups were synthesized and screened for in vitro antiplasmodial activity against Plasmodium falciparum (3D7) using the [³H] hypoxanthine incorporation inhibition assay. Chalcones with 2,2,2-trifluoroethoxy groups substituted on the p- and m-positions of the 1-phenyl ring showed weak antiplasmodial activity, while compounds substituted on the o-position of the 1-phenyl ring displayed enhanced antiplasmodial activity, thus indicating that 2,2,2-trifluoroethoxy groups on the 1-phenyl ring of chalcones show position-dependent antiplasmodial activity. Of the 34 compounds synthesized, chalcones 3a and 3f exhibited significant inhibitory effects, with IC50 values of 3.0 μg/mL and 2.2 μg/mL, respectively. Moreover, these compounds 3a and 3f showed profound antiplasmodial activity in combination with artemisinin in vitro. The most active molecules, 3a, and 3f, were further assessed for their cytotoxicity towards mammalian Vero cells and the selectivity index (SI) values are 8.6, and 8.2 respectively, being considered non-toxic. We also studied the antiplasmodial activity of 2-fluoroethoxychalcones to discern the effect of the...Continue Reading

References

Apr 29, 1994·Journal of Medicinal Chemistry·P M O'NeillB K Park
Mar 27, 2001·Annual Review of Pharmacology and Toxicology·B K ParkP M O'Neill
Aug 30, 2001·European Journal of Medicinal Chemistry·J N DomínguezP J Rosenthal
Jul 13, 2002·Bioorganic & Medicinal Chemistry Letters·Javier RojasM Luisa Ferrándiz
Apr 23, 2004·Organic Letters·Jingjun YinMark A Huffman
May 4, 2004·Chembiochem : a European Journal of Chemical Biology·Peter Jeschke
Jan 12, 2005·European Journal of Medicinal Chemistry·Shen-Jeu WonChun-Nan Lin
Nov 9, 2005·European Journal of Medicinal Chemistry·Alain VallaPierre Potier
Mar 10, 2007·Current Medicinal Chemistry·Alka Mital
Sep 11, 2007·Bioorganic & Medicinal Chemistry·Masahiro OnoMorio Nakayama
Jan 17, 2008·Chemical Society Reviews·Sophie PurserVéronique Gouverneur
Dec 10, 2008·Acta Tropica·Lokesh C MishraVirendra K Bhasin
Mar 10, 2009·European Journal of Medicinal Chemistry·Amit BhattacharyaVirendra K Bhasin
Dec 4, 2012·European Journal of Medicinal Chemistry·Naveen Kumar KonduruNaseem Ahmed
Feb 21, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ana GilIgnacio Aldana
Aug 21, 2014·Recent Patents on Anti-cancer Drug Discovery·Chandrabose KarthikeyanPiyush Trivedi
Jul 21, 2015·ACS Medicinal Chemistry Letters·Koneni V SashidharaMukesh Pasupuleti
May 25, 2016·Bioorganic & Medicinal Chemistry Letters·Serdar BurmaogluNizami Duran
Aug 2, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Marcelo N GomesBruno J Neves
Aug 12, 2017·European Journal of Medicinal Chemistry·Yuan-Qiang HuFeng Zhao

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column chromatography

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