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Molecules 2009, 14(4), 1483-1494; doi:10.3390/molecules14041483
Article

Synthesis of Novel Hybrid Molecules from Precursors With Known Antiparasitic Activity

1,* , 2 and 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
* Authors to whom correspondence should be addressed.
Received: 4 March 2009 / Revised: 2 April 2009 / Accepted: 7 April 2009 / Published: 9 April 2009
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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 Hybrid Molecules; Metronidazole; Chloroquine; Entamoeba Histolytica; Giardia Intestinalis
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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