Synthesis, characterization and cytotoxic activity of new salicylaldehyde benzoylhydrazone derivatives as potential anti-proliferative agents

Abstract

Three new hydrazones, derivatives of salicylaldehyde benzoylhydrazone, were synthesized as potential anti-proliferative compounds. The structure of the new compounds was characterized by elemental and thermo-gravimetric analyses, IR, 1H and 13C-NMR spectroscopy and quantum chemical calculations. The cytotoxic effects of new hydrazones were examined on a wide spectrum of human tumor cell lines. The obtained results revealed that all compounds proved to be equipotent or moreactive than cisplatin, and far more activethan another utilized anticancer drug, melphalan. On the basis of IC50 values the compound 3-methoxy-salicylaldehyde isonicotinoylhydrazone (mSIH) was found to be the most active cytotoxic agent at all cell lines.

3-methoxy aroylhydrazones – free radicals scavenging, anticancer and cytoprotective potency

“…The three derivatives of SBH studied in the present work -3-methoxysalicylaldehyde benzoylhydrazone (3mSBH), 3-methoxysalicylaldehyde-4-hydroxybenzoylhydrazone (3mShBH) and 3-methoxysalicylaldehyde isonicotinoylhydrazone (3mSIH)were previously synthesized and structurally characterized by elemental, thermo-gravimetric analyses, IR, 1 H and 13 C-spectroscopy [13]. The compounds were obtained by the Schiff-base condensation method (Scheme 1).…”

“…Some investigations have proved that the structural characteristics of aroylhydrazones turn them into promising candidates for the development of novel synthetic antioxidants retarding the cellular damage induced by free radicals [11,12]. Aroylhydrazones derived from salicylaldehyde are biologically active molecules and one of the most interesting compounds is salicylaldehyde benzoylhydrazone (SBH) which has been proved to inhibit the process of DNA synthesis and cell growth of malignant cells in vitro and in vivo [6,13].…”

“…Recently, our group synthesized a series of structurally similar hydrazones by the Schiff-base condensation between 3-methoxysalicylaldehyde and different benzhydrazides [13]. Knowing the powerful antioxidant properties of the phenolic compounds and the remarkable activity of isoniazid itself, we chose to explore three hydrazones derived by benzhydrazide, 4-hydroxybenzhydrazide and isonicotinoyl hydrazide and consequently to compare how the replacement of an H-atom on 4th position in hydrazide affects the antioxidant properties and cytotoxic effect.…”

Gallium (III) Complexes with 5-Bromosalicylaldehyde Benzoylhydrazones: In Silico Studies and In Vitro Cytotoxic Activity

“…The additional hydroxy group in the aldehyde part increases the number of donor atoms and enhances the coordination ability of the ligands. Various derivative aldehydes have been used in order to discover new biologically active compounds [ 3 , 4 , 5 , 6 , 7 ]. Pyridoxal isonicotinyl hydrazone (PIH), salicylaldehyde benzoyl hydrazone (SBH), and their analogues are used as chelating agents for reducing the toxic effects of iron-overload diseases, such as β-thalassemia [ 4 , 8 , 9 , 10 , 11 , 12 ].…”

Cancer cell growth inhibition by aroylhydrazone derivatives

“…For example, one of the compounds, salicylaldehyde benzoylhydrazone (SBH), has been shown to inhibit DNA synthesis and cell growth in a variety of cultured human and rodent cells [25]. Various derivatives of SBH with a number of functional groups have been created in recent years, in order to discover new bioactive compounds with high antitumour activity and minimal toxicity [26][27][28][29][30][31][32][33].…”