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Relevant articles and documents
Synthesis of novel hybrid molecules from precursors with known antiparasitic activity
Saadeh, Haythem A. Mosleh, Ibrahim M. Mubarak, Mohammad S.
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 K 2CO3 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.
Synthesis and evaluation of a boronated nitroimidazole for boron neutron capture therapy
Swenson, David H. Laster, Brenda H. Metzger, Robert L.
We postulated that nitroimidazoles, previously used for radiosensitizing solid tumors, may be interesting templates as carriers of 10B for boron neutron capture therapy. To test this hypothesis, we synthesized a 10B- enriched nitroimidazole, 1-[2-[(undecahydro-closo-dodecaborato)thio]ethyl]- 2-methyl-5-nitroimidazole (imidocaptate), by coupling the Cs salt of BSH (Cs210B12H11SH) with 1-(2-bromoethyl)-2-methyl-5-nitroimidazole followed by purification of the adduct. Imidocaptate was taken up by V-79 cells in culture and showed no inherent toxicity under euoxic conditions up to 1.05 mM (126 μg of 10B/mL of culture medium). Imidocaptate showed a dose-dependent decrease in D(o) when the treated cells were irradiated with a thermal neutron beam. At the highest dose tested (126 μg of 10B/mL of culture medium), the ratio of control to sample D(o) values was 2.6 for both linear quadratic and single-hit multitarget models. At 33 μg of 10B/mL, imidocaptate showed a control/treated Do ratio (1.5) equal to that observed with the disulfide form of BSH at 28 μg of 10B/mL. Compared to BSH and its disulfide, the reduced toxicity and equipotency of imidocaptate suggest that this agent may be useful for boron neutron capture therapy of cancer.
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