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New Synthesis and Antiparasitic Activity of Model 5-Aryl-1-methyl-4-nitroimidazoles
Chemistry Department, Faculty of Science, University of Jordan, Amman 11942, Jordan
Department of Biological Sciences, Faculty of Science, University of Jordan, Amman 11942, Jordan
* Author to whom correspondence should be addressed.
Received: 3 July 2009; in revised form: 19 July 2009 / Accepted: 23 July 2009 / Published: 27 July 2009
Abstract: A number of 5-aryl-1-methyl-4-nitroimidazoles 5a-f have been synthesized in good yields by the Suzuki coupling reaction between 5-chloro-1-methyl-4-nitroimidazole (3) and arylboronic acids 4a-f, aided by dichlorobis-(triphenylphosphine)palladium(II), K2CO3, and tetrabutylammonium bromide in water at 70-80 °C. Compounds 5a-f were characterized by elemental analysis, NMR and MS spectral data. On the basis of in vitro screening data, 5-(3-chlorophenyl)-1-methyl-4-nitro-1H-imidazole (5f)exhibited potent lethal activity against Entamoeba histolytica and Giardia intestinalis with IC50 = 1.47 µM/mL, a value lower by a factor of two than that of the standard drug, metronidazole. The boosted activity of 5f was not accompanied by any increased cytotoxicity.The rest of the series also exhibited potent antiparasitic activity with IC50 valuesin the 1.72-4.43 µM/mL range. The cytotoxicity of the derivatives 5c and 5e was increased compared to the precursor compound, metronidazole, although they remain non-cytotoxic at concentrations much higher than the antiparasitic concentration of the two derivatives.
Keywords: 5-chloro-1-methyl-4-nitroimidazole; arylboronic acids; Suzuki coupling; 5-aryl-1-methyl-4-nitroimidazoles; antiparasitic activity
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Saadeh, H.A.; Mosleh, I.M.; El-Abadelah, M.M. New Synthesis and Antiparasitic Activity of Model 5-Aryl-1-methyl-4-nitroimidazoles. Molecules 2009, 14, 2758-2767.
Saadeh HA, Mosleh IM, El-Abadelah MM. New Synthesis and Antiparasitic Activity of Model 5-Aryl-1-methyl-4-nitroimidazoles. Molecules. 2009; 14(8):2758-2767.
Saadeh, Haythem A.; Mosleh, Ibrahim M.; El-Abadelah, Mustafa M. 2009. "New Synthesis and Antiparasitic Activity of Model 5-Aryl-1-methyl-4-nitroimidazoles." Molecules 14, no. 8: 2758-2767.