Next Article in Journal
Synthesis of N-Substituted 5-Iodouracils as Antimicrobial and Anticancer Agents
Previous Article in Journal
Wet Aerobic Oxidation of Lignin into Aromatic Aldehydes Catalysed by a Perovskite-type Oxide: LaFe1-xCuxO3 (x=0, 0.1, 0.2)
Article

New Synthesis and Antiparasitic Activity of Model 5-Aryl-1-methyl-4-nitroimidazoles

1
Chemistry Department, Faculty of Science, University of Jordan, Amman 11942, Jordan
2
Department of Biological Sciences, Faculty of Science, University of Jordan, Amman 11942, Jordan
*
Author to whom correspondence should be addressed.
Molecules 2009, 14(8), 2758-2767; https://doi.org/10.3390/molecules14082758
Received: 3 July 2009 / Revised: 19 July 2009 / Accepted: 23 July 2009 / Published: 27 July 2009
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. View Full-Text
Keywords: 5-chloro-1-methyl-4-nitroimidazole; arylboronic acids; Suzuki coupling; 5-aryl-1-methyl-4-nitroimidazoles; antiparasitic activity 5-chloro-1-methyl-4-nitroimidazole; arylboronic acids; Suzuki coupling; 5-aryl-1-methyl-4-nitroimidazoles; antiparasitic activity
Show Figures

Graphical abstract

MDPI and ACS Style

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. https://doi.org/10.3390/molecules14082758

AMA Style

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. https://doi.org/10.3390/molecules14082758

Chicago/Turabian Style

Saadeh, Haythem A., Ibrahim M. Mosleh, and Mustafa M. El-Abadelah 2009. "New Synthesis and Antiparasitic Activity of Model 5-Aryl-1-methyl-4-nitroimidazoles" Molecules 14, no. 8: 2758-2767. https://doi.org/10.3390/molecules14082758

Find Other Styles

Article Access Map by Country/Region

1
Only visits after 24 November 2015 are recorded.
Back to TopTop