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Issue 14, 2010
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One-pot double intramolecular homolytic aromatic substitution routes to dialicyclic ring fused imidazobenzimidazolequinones and preliminary analysis of anticancer activity

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Abstract

Bu3SnH/1,1′-azobis(cyclohexanecarbonitrile) (ACN)-mediated five, six, and seven-membered double alkyl radical cyclizations onto imidazo[5,4-f]benzimidazole and imidazo[4,5-f]benzimidazole are described. The quinone derivatives evaluated show selective toxicity towards human cervical (HeLa) and prostate (DU145) cancer cell lines (with negligible toxicity towards a normal human cell line, GM00637). Only the Fremy oxidation of the 6-aminoimidazo[5,4-f]benzimidazole gave iminoquinone, which showed high specificity towards the prostate cancer cell line (DU145).

Graphical abstract: One-pot double intramolecular homolytic aromatic substitution routes to dialicyclic ring fused imidazobenzimidazolequinones and preliminary analysis of anticancer activity

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Publication details

The article was received on 24 Feb 2010, accepted on 20 Apr 2010 and first published on 18 May 2010


Article type: Paper
DOI: 10.1039/C003511D
Citation: Org. Biomol. Chem., 2010,8, 3149-3156
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    One-pot double intramolecular homolytic aromatic substitution routes to dialicyclic ring fused imidazobenzimidazolequinones and preliminary analysis of anticancer activity

    V. Fagan, S. Bonham, M. P. Carty and F. Aldabbagh, Org. Biomol. Chem., 2010, 8, 3149
    DOI: 10.1039/C003511D

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