Synthesis of novel hybrid molecules from precursors with known antiparasitic activity

Molecules. 2009 Apr 9;14(4):1483-94. doi: 10.3390/molecules14041483.

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 K(2)CO(3) 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 IC(50) (about 1 microM) was lower, at least by a factor of five, compared to the standard drug, metronidazole. In addition, the IC(50) 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 IC(50 values) of about 5.5 microM, and 140 microM, respectively, against the tested parasites. These two hybrid molecules, 8, 10-a, were also non-cytotoxic at the lethal concentrations against the parasites.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylamides / chemical synthesis
  • Acrylamides / chemistry
  • Animals
  • Antiparasitic Agents / chemical synthesis*
  • Antiparasitic Agents / chemistry
  • Antiparasitic Agents / pharmacology*
  • Cell Line
  • Entamoeba histolytica / drug effects*
  • Giardia lamblia / drug effects*
  • Humans
  • Molecular Structure
  • Nitrofurans / chemical synthesis
  • Nitrofurans / chemistry
  • Nuclear Magnetic Resonance, Biomolecular
  • Quinolines / chemical synthesis
  • Quinolines / chemistry

Substances

  • Acrylamides
  • Antiparasitic Agents
  • Nitrofurans
  • Quinolines