Org Biomol Chem. 2010 Jul 21;8(14):3149-56. Epub 2010 May 18.

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

Fagan V, Bonham S, Carty MP, Aldabbagh F.

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School of Chemistry, National University of Ireland, Galway, Ireland.

Abstract

Bu(3)SnH/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).

PMID:: 20485753; [PubMed - indexed for MEDLINE]

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