Azino-Fused Benzimidazolium Salts as DNA Intercalating Agents. 2.
The Journal of Organic Chemistry1997Vol. 62(16), pp. 5476–5483
Citations Over TimeTop 10% of 1997 papers
Joaquı́n Pastor, Jorge G. Siro, José L. García‐Navío, Juan J. Vaquero, Julio Álvarez‐Buílla, Federico Gago, Beatriz de Pascual‐Teresa, Manuel Pastor, Ma. Mercedes T. Rodrigo
Abstract
The synthesis of new pyrido[1,2-a]- and pyridazino[1,6-a]benzimidazolium salts by basic condensation of 1,3-disubstituted 2-alkylbenzimidazolium salts and 1,2-diketones and subsequent chemical transformations is described. The DNA-binding properties were examined by UV-vis spectroscopy, viscosimetric determinations, and molecular modeling techniques. The presence of a flat polycyclic hydrocarbon moiety such as a naphthalene-1,8-diyl or a biphenyl-o,o'-diyl, fused to the cationic heterocycle, appears to enhance the interaction with DNA. Variation of the substituents on the indole-like N will allow us to build up a new series of bis-salts with bis-intercalating properties.
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