Resveratrol-based Schiff base derivatives: Synthesis, characterization and cytotoxic study

Abstract

New resveratrol-based Schiff base derivatives (1,2,4-triazole Schiff base derivatives 5a-d and hydrazide Schiff base derivatives 7a-d) were designed, synthesized via Schiff base reaction in the presence of H2SO4 as a catalyst in yield (91.13–41.79 %), and characterized by FTIR, 1H NMR, 13C NMR, DEPT-135 and high-resolution mass HRMS (ESI + ) spectroscopy techniques. A cytotoxicity (MTT) assay was applied to determine the cytotoxic activity of the target compounds on three human cells (HepG2, MCF-7, and T47D). The bioassay showed that a majority of target derivatives showed superior inhibitory activity than the parent compound resveratrol. Among them, derivative 7d showed the best cytotoxic activity against breast cancer cell lines (MCF-7 and T47D) (IC50 = 24.62 and 70.92 μM, respectively). Also, derivative 7b exhibited the best cytotoxic activity against the liver cancer cell line HepG2 (IC50 = 67.47 μM) compared to the parent compound resveratrol. These preliminary findings suggest that the resveratrol-based hydrazide Schiff base derivatives are promising anticancer agents that inspire further developments in this area.

Keywords

• Resveratrol
• Schiff base
• Hydrazide
• 1,2,4-Triazole
• Cytotoxicity
• MTT assay