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Synthesis and antitumor activity of aza-brazilan derivatives containing imidazolium salt pharmacophore

Abstract

The synthesis of a series of novel aza-brazilan derivatives containing imidazolium salt pharmacophores is presented. Biological activity of such imidazolium salts was further evaluated in vitro against a panel of human tumor cell lines. The results suggest that the electron-withdrawing group on the aza-brazilan moiety, substituted 5,6-dimethyl-benzimidazoless ring and substitution of the imidazolyl-3-position with a 4-methylbenzyl group were essential for modulating cytotoxic activity. Compounds 55 and 39, bearing a 4-methylbenzyl substituent at position-3 of 5,6-dimethyl-benzimidazole, were found to be the most potent compounds with IC50 values of 0.52-1.30 μM and 0.56-1.51 μM against four human tumor cell lines investigated. Particularly, compound 57 exhibited inhibitory activity against MCF-7 cell line with IC50 value of 0.35 μM and 56-fold more sensitive to DDP. Moreover, compound 55 inhibited cell proliferation through inducing the G0/G1 cell cycle arrest and apoptosis in SMMC-7721 cells.

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Supplementary files

Publication details

The article was received on 22 Feb 2019, accepted on 07 May 2019 and first published on 10 May 2019


Article type: Research Article
DOI: 10.1039/C9MD00112C
Med. Chem. Commun., 2019, Accepted Manuscript

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    Synthesis and antitumor activity of aza-brazilan derivatives containing imidazolium salt pharmacophore

    M. Huang, S. Duan, X. Ma, B. Cai, D. Wu, Y. Li, L. Li, H. Zhang and X. Yang, Med. Chem. Commun., 2019, Accepted Manuscript , DOI: 10.1039/C9MD00112C

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