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

• Published in: Results in Chemistry 2024-01, Vol.7, p.101516, Article 101516
• Main Authors: Al-lehaib, Lamya A., Ali, Ehab M.M., Al-Footy, Khalid O., Al-Ghamdi, Huda A., Al-Zahrani, Fatimah A.M., Al-Amshany, Z.M., El-Shishtawy, Reda M.
• Format: Article
• Language: English
• Subjects: 1,2,4-Triazole; Cytotoxicity; Hydrazide; MTT assay; Resveratrol; Schiff base
• ISSN: 2211-7156; 2211-7156
• DOI: 10.1016/j.rechem.2024.101516

[Display omitted] •New stilbene-based Schiff base derivatives have been designed and synthesized, and their anticancer activities against (HepG2,MCF-7,andT47D) cell lines were evaluated.•The majority of derivatives have higher inhibitory activity than parent compound resveratrol.•Compound (7d) showed the best potent cytotoxicity against breast cancer (MCF-7andT47D).•Compound (7d) exhibited the most potent cytotoxicity against liver cancer (HepG2). 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.