Effect of fluorine substituents in 4-(1-benzyl-1H-benzo[d]imidazol-2-yl)thiazole for the study of antiparasitic treatment of cysticercosis on a Taenia crassiceps model†

Abstract

This work details the synthesis of five N-benzylated derivatives of thiabendazoles (L1–L5), four of which were previously unreported in the literature (L2–L5). The compounds were characterised using a comprehensive array of spectroscopic (FT-IR, ¹H, ¹³C{1H}, and ¹⁹F{1H} NMR), spectrometric (MS-EI+) and diffractometric (SC-DRX) techniques. To evaluate the effect of increased fluorine substituents in the N-benzyl fragment, we conducted a parasitotoxic activity assay, testing the compounds at various concentrations of unhatched Taenia crassiceps cysticerci. The inclusion of the N-benzyl fragment and the increase in fluorine substituents led to an enhancement in the lipophilicity of thiabendazoles.