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

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).

• Authors: Vincent Fagan, Sarah Bonham, Michael P Carty, Fawaz Aldabbagh
• Journal: Organic & biomolecular chemistry (Org Biomol Chem) Vol. 8 Issue 14 Pg. 3149-56 (Jul 21 2010) ISSN: 1477-0539 [Electronic] England
• PMID: 20485753 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents
• Benzimidazoles

Topics

• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Benzimidazoles (chemical synthesis, chemistry, pharmacology)
• Cell Line, Tumor
• Humans
• Inhibitory Concentration 50