New synthesis and antiparasitic activity of model 5-aryl-1-methyl-4- nitroimidazoles

Haythem A. Saadeh, Ibrahim M. Mosleh, Mustafa M. El-Abadelah

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

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), K 2CO 3, 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 IC 50 = 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 IC 50 values in 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.

Original languageEnglish
Pages (from-to)2758-2767
Number of pages10
JournalMolecules
Volume14
Issue number8
DOIs
Publication statusPublished - Aug 2009
Externally publishedYes

Keywords

  • 5-aryl-1-methyl-4-nitroimidazoles
  • 5-chloro-1-methyl-4-nitroimidazole
  • Antiparasitic activity
  • Arylboronic acids
  • Suzuki coupling

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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