new synthesis and antiparasitic activity of model 5-aryl-1-methyl-4-nitroimidazoles新的模型5-aryl-1-methyl-4-nitroimidazoles合成和抗寄生物的活动.pdfVIP

Molecules 2009, 14, 2758-2767; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article New Synthesis and Antiparasitic Activity of Model 5-Aryl-1- methyl-4-nitroimidazoles Haythem A. Saadeh 1,*, Ibrahim M. Mosleh 2 and Mustafa M. El-Abadelah 1 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; E-mail: h.saadeh@.jo; Tel. +962 6 5355000, ext. 22159; Fax: +962 6 5348932 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), K CO and tetrabutylammonium bromide in water at 70-80 °C. Compounds 5a-f were 2 3, 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