Novel styryl-heterocyclic hybrids: Synthesis, characterization and anticancer activity

Abstract

Novel styryl-heterocyclic hybrids were designed and synthesized via Knoevenagel condensation reaction between 4-(4-((5-(((4-methyl-2-oxo-2H-chromen-7-yl)oxy)methyl)-1,3,4-oxadiazol-2-yl)methyl)piperazin-1-yl)benzaldehyde and indolenine (very good yield 85.79–91.64 %) or quinoline (fair yield 43.15 %) derivatives. The synthesized compounds were characterized by spectroscopic techniques: FTIR, 1H NMR, 13C NMR, DEPT-135, and high-resolution mass HRMS (ESI+). All target compounds were evaluated for their anticancer activity against three human cells (HepG2, MCF-7, and T47D) using the MTT assay in vitro. The bioassay showed that all target compounds exhibited superior inhibitory activity than the parent compound resveratrol and lower than the reference drug (cisplatin). Among them, compound 10d showed the best cytotoxic activity against HepG2 (IC50 = 11.80 μM) and MCF-7 (IC50 = 24.55 μM). In addition, compound 10c displayed the best cytotoxic activity against T47D (IC50 = 43.24 μM) in comparison to the parent compound resveratrol. Based on these findings, the indolenine-based styryl scaffold is a novel chemotype for developing anticancer drugs, so further investigation is necessary.

Keywords

• Styryl-heterocyclic hybrids
• Indolenine
• Quinoline
• Anticancer activity
• MTT assay