Synthesis and antitumor activity of novel N-substituted tetrahydro-β-carboline–imidazolium salt derivatives. Issue 39 (19th September 2016)

• Record Type: Journal Article
• Authors: Zhou, Bei; Liu, Zheng-Fen; Deng, Guo-Gang; Chen, Wen; Li, Min-Yan; Yang, Li-Juan; Li, Yan; Yang, Xiao-Dong; Zhang, Hong-Bin
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 39(2016)
• Page Start: 9423
• Page End: 9430
• Publication Date: 2016-09-19
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob01495j
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A series of novel N -substituted tetrahydro-β-carboline imidazolium salt derivatives were synthesized and their antitumor structure–activity relationship studies were reported. Abstract : The synthesis of a series of novel N -substituted tetrahydro-β-carboline–imidazolium salt derivatives is presented. The biological properties of the compounds were evaluated in vitro against a panel of human tumor cell lines. The results suggest that the benzimidazole ring and 1-(naphthalen-2-yl)ethan-1-one or 2-naphthylmethyl substituent at the imidazolyl-3-position were vital for modulating cytotoxic activity. Compound41 was observed as a potent derivative with IC50 values of 3.24–8.78 μM and exhibited cytotoxic activity selectively against HL-60, A-549 and MCF-7 cell lines. Meanwhile, high inhibitory activities selectively against HL-60 and MCF-7 cell lines were observed for compound51 . Moreover, compound51 was able to induce G1 phase cell cycle arrest and apoptosis in MCF-7 cells. The cytotoxicity of compound51 against human normal lung epithelial cell line BEAS-2B was further evaluated.