1H-benzimidazole-2-yl hydrazones as tubulin-targeting agents: Synthesis, structural characterization, anthelmintic activity and antiproliferative activity against MCF-7 breast carcinoma cells and molecular docking studies

New 1H-benzimidazole-2-yl hydrazones with combined antiparasitic and antioxidant activity

“…The shift of OH group from 4- to 3-position to give hydrazone 5b led to further increase in activity (100% efficacy at a concentration of 50 μg ml −1 ). In accordance with these and our earlier results, 18 it can be assumed that the presence of a OH group in the 3-position of the phenyl moiety of the molecule accounts for a larger share of the anti- Trichinella spiralis activity. The benzimidazolyl-2-hydrazone of 2,3-dihydroxybenzaldehyde (compound 5b) and of 3,4-dihydroxybenzaldehyde (compound 5d), respectively, killed the total parasitic larvae (100% effectiveness after 24 hour incubation period at 37 °C) in concentrations of 50 μg ml −1 .…”

“…Based on the in vitro activity of hydrazones 5a-l on T. spiralis ML as well as that of other recently investigated 1 H -benzimidazolyl-2-hydrazones, 18 it was outlined that the combination of benzimidazole and hydrazone pharmacophores in addition with hydroxyl and/or methoxyl groups on the arylidene moiety favorably modulates the anti- Trichinella spiralis activity. Indeed, the studied benzimidazole hydrazones showed remarkable larvicidal effect superior to the benzimidazole-containing derivatives earlier synthesized by us.…”

“…On the other hand, in our previous paper, 18 we reported the synthesis of a series of benzimidazolyl-2-hydrazones of fluoro-, hydroxy- and methoxy-substituted benzaldehydes and 1,3-benzodioxole-5-carbaldehyde ( Fig. 1 ).…”

“…The benzimidazoles showed potent anthelmintic activity against isolated muscle larvae of T. spiralis in an in vitro experiment as well as moderate antiproliferative activity against MCF-7 breast cancer cells. 18 The antiparasitic and anticancer effects were correlated to the ability of the compounds to interfere with tubulin polymerization, as demonstrated by in vitro testing. As a next step in our research 18 and on the basis of the above mentioned facts, the present study reports the synthesis of a new series of 1 H -benzimidazol-2-yl hydrazones containing hydroxyphenyl and methoxyphenyl moieties, their anthelmintic activity as well as antioxidant and radical scavenging properties determined using in vitro assays – DPPH, ABTS, and iron induced oxidative damage in model systems containing lecithin and deoxyribose.…”

“… 18 The antiparasitic and anticancer effects were correlated to the ability of the compounds to interfere with tubulin polymerization, as demonstrated by in vitro testing. As a next step in our research 18 and on the basis of the above mentioned facts, the present study reports the synthesis of a new series of 1 H -benzimidazol-2-yl hydrazones containing hydroxyphenyl and methoxyphenyl moieties, their anthelmintic activity as well as antioxidant and radical scavenging properties determined using in vitro assays – DPPH, ABTS, and iron induced oxidative damage in model systems containing lecithin and deoxyribose. In order to rationalize the observed effects, a detailed computational study of the radical scavenging properties using density functional theory (DFT) was carried out.…”