ZnO nanoparticles catalyzed synthesis of bis- and poly(imidazoles) as potential anticancer agents

Abstract

A synthesis of bis- and poly(imidazoles) by one-pot three-component reaction of 1,2-diketone with aldehydes and ammonium acetate in the presence of catalytic amount of ZnO nanocatalyst is reported. The reactions were performed under conventional heating as well as under microwave irradiation. The anticancer activities of the synthesized compounds were evaluated against human breast adenocarcinoma cell line (MCF-7), liver cancer cell line (HepG-2), and epithelial colorectal adenocarcinoma cells (CaCO-2). The results of the cytotoxic activity revealed that compound 16 b with bis(imidazole) analog that incorporated a 4,5-difuran rings was potent against HepG-2 cancer cells (IC₅₀ = 8.14 µM) with high selectivity index (SI = 27.47). Compound 25 incorporating four imidazole units was active against MCF-7 cell line (IC₅₀ = 12.62 µM) and showed a significant selectivity index (SI = 7.71). Moreover, compound 27 containing six imidazole units exhibited the highest activity against the CaCO-2 cell line (IC₅₀ = 32.51 μM) with SI = 4.09.

Graphical Abstract

Keywords:

• Bis(imidazoles)
• cytotoxic activity
• docking study
• poly(imidazoles)
• ZnO nanocatalyst