Novel 3-substituted fluorine imidazolium/triazolium salt derivatives: synthesis and antitumor activity

Abstract

A series of novel (±)-3-substituted fluorene–imidazolium/triazolium salt derivatives has been prepared and evaluated in vitro against a panel of human tumor cell lines. The results suggest that the existence of 2-methyl-benzimidazole or 5,6-dimethyl-benzimidazole rings and substitution of the imidazolyl/triazolyl-3/4-position with a naphthylacyl or 4-methoxyphenacyl group were important for modulating cytotoxic activity. Compounds 37 and 42 were found to be the most potent derivatives with IC₅₀ values of 0.51–2.51 μM and exhibited cytotoxic activities selectively against myeloid leukaemia (HL-60), liver carcinoma (SMMC-7721) and lung carcinoma (A549). Compound 37 can remarkably induce the G2/M phase cell cycle arrest and apoptosis in SMMC-7721 cells. Additionally, compound 30 exhibited selective cytotoxicity to some extent between cancer cells (A549) and normal cells (BEAS-2B).