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Mary Lynch, Sarah Hehir, Paul Kavanagh, Dónal Leech, John O'Shaughnessy, Michael P. Carty and Fawaz Aldabbagh Synthesis by Radical Cyclization and Cytotoxicity of Highly Potent Bioreductive Alicyclic Ring Fused [1,2-a]Benzimidazolequinones Chemistry - A European Journal 13

Version of Record online: 2 JAN 2007 | DOI: 10.1002/chem.200601450

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Tributyltin hydride (Bu3SnH)-mediated homolytic aromatic substitutions of nucleophilic N-alkyl radicals onto the benzimidazole 2-position were carried out by quaternising the pyridine-like N-3 of imidazole with camphorsulfonic acid (CSA) and by using a large excess of 1,1′-azobis(cyclohexanecarbonitrile) (ACN; see scheme) to supplement the non-chain reaction. The IC50 values for the cytotoxicity of benzimidazolequinones towards the human skin fibroblast cell line GM00637 were in the nanomolar range, as determined by using the MTT assay.

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