New 1H-benzimidazole-2-yl hydrazones with combined antiparasitic and antioxidant activity
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2021-12-14
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Abstract
Parasitic infections, caused mainly by the speciesTrichinella spiralis(T. spiralis), are widespread around the world and lead to morbidity and mortality in the population. Meanwhile, some studies have showed that these parasites induce oxidative stress in the infected host. With the aim of developing a class of compounds combining anthelmintic with antioxidant properties, a series of new benzimidazolyl-2-hydrazones5a-l, bearing hydroxyl- and methoxy-groups, were synthesized. The anthelmintic activity on encapsulatedT. spiraliswas studiedin vitrothus indicating that all hydrazones were more active than the clinically used anthelmintic drugs albendazole and ivermectin.5band5dkilled the total parasitic larvae (100% effectiveness) after 24 hours incubation period at 37 °C in both concentrations (50 and 100 μg ml−1). The antioxidant activity of the target compounds was elucidatedin vitroagainst stable free radicals DPPH and ABTS as well as iron induced oxidative damage in model systems containing biologically relevant molecules lecithin and deoxyribose. The two 2,3- and 3,4-dihydroxy hydrazones5band5dwere the most effective radical scavengers in all studied systems. DFT calculations were applied to calculate the reaction enthalpies in polar and nonpolar medium and estimate the preferred mechanism of antioxidant activity. The relative radical scavenging ability of compounds5a-lshowed a good correlation to the experimentally observed trends. It was found that the studied compounds are capable to react with various free radicals - ˙OCH3, ˙OOH and ˙OOCH3, through several possible reaction pathways - HAT in nonpolar medium, SPLET in polar medium and RAF in both media.