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Synthesis of Novel Hybrid Molecules from Precursors With Known Antiparasitic Activity
Chemistry Department, Faculty of Science, University of Jordan, Amman 11942, Jordan
Department of Biological Sciences, Faculty of Science, University of Jordan, Amman 11942, Jordan
* Authors to whom correspondence should be addressed.
Received: 4 March 2009; in revised form: 2 April 2009 / Accepted: 7 April 2009 / Published: 9 April 2009
Abstract: Three novel new compounds derived from antiparasitic precursors have been synthesized and tested for their antiamoebic and antigiardial activities. The condensation of 2-(2-methyl-5-1H-nitroimidazolyl)ethylamine (6) with 5-nitro-2-furylacrylic acid (7) gave 3-(5-nitrofuran-2-yl)-N-[2-(5-nitroimidazol-1-yl)ethyl]acrylamide (8). Condensation of 7 with 7-chloro-4-(piperazin-1-yl)quinoline (9) afforded 1-[4-(7-chloroquinolin-4-yl)piperazin-1-yl)-3-(5-nitrofuran-2-yl)propenone as a mixture of two isomers; 10-a (the E-isomer) and 10-b (the Z-isomer). In addition, the reaction of 9 with 1-(2-bromoethyl)-2-methyl-5-nitroimidazole (11) in the presence of K2CO3 and NaI yielded 7-chloro-4-(4-[2-(5-nitroimidazol-1-yl)ethyl]-piprazin-1-yl)quinoline (12). On the basis of preliminary screening data for these new compounds, compound 12 exhibited potent lethal activities against Entamoeba histolytica and Giardia intestinalis; its IC50 ( about 1 µM) was lower, at least by a factor of five, compared to the standard drug, metronidazole. In addition, the IC50 of compound 12 against the tested parasites is 600 times below that against Hep-2 and Vero cells. Compounds 8 and 10-a also exhibited potent or moderate antiamoebic and antigiardial activities with IC50 values of about 5.5 µM, and 140 µM, respectively, against the tested parasites. These two hybrid molecules, 8, 10-a, were also non-cytotoxic at the lethal concentrations against the parasites.
Keywords: Hybrid Molecules; Metronidazole; Chloroquine; Entamoeba Histolytica; Giardia Intestinalis
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MDPI and ACS Style
Saadeh, H.A.; Mosleh, I.M.; Mubarak, M.S. Synthesis of Novel Hybrid Molecules from Precursors With Known Antiparasitic Activity. Molecules 2009, 14, 1483-1494.
Saadeh HA, Mosleh IM, Mubarak MS. Synthesis of Novel Hybrid Molecules from Precursors With Known Antiparasitic Activity. Molecules. 2009; 14(4):1483-1494.
Saadeh, Haythem A.; Mosleh, Ibrahim M.; Mubarak, Mohammad S. 2009. "Synthesis of Novel Hybrid Molecules from Precursors With Known Antiparasitic Activity." Molecules 14, no. 4: 1483-1494.