Synthesis and DNA Binding Properties of γ-Carbolinium Derivatives and Benzologues

The 5H-pyrido[4,3-b]indole, 11H-indolo[3,2-c]quinoline, 5H-benzo[f]pyrido[4,3-b]indole, and 13H-benz[5,6]indolo[3,2-c]quinoline heteroaromatic nuclei have been synthesized by the Graebe−Ullmann method by classical heating or under microwave irradiation. These tri-, tetra-, and pentacyclic compounds...

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Bibliographic Details
Published in:Journal of organic chemistry 1996-08, Vol.61 (16), p.5587-5599
Main Authors: Molina, Andrés, Vaquero, Juan J, Garcia-Navio, José L, Alvarez-Builla, Julio, de Pascual-Teresa, Beatriz, Gago, Federico, Rodrigo, María M, Ballesteros, Milagros
Format: Article
Language:English
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Summary:The 5H-pyrido[4,3-b]indole, 11H-indolo[3,2-c]quinoline, 5H-benzo[f]pyrido[4,3-b]indole, and 13H-benz[5,6]indolo[3,2-c]quinoline heteroaromatic nuclei have been synthesized by the Graebe−Ullmann method by classical heating or under microwave irradiation. These tri-, tetra-, and pentacyclic compounds were transformed into the corresponding cationic derivatives by N-alkylation, and the DNA-binding properties of the resulting cationic systems were examined using UV−vis spectroscopy, viscometric determinations, and molecular modeling techniques. The tetracyclic cations were transformed into bis-salts by means of a diethyl bispiperidine rigid chain and a more flexible polyamide linker, but the low solubility of these bis-salts made the study of their bisintercalating properties difficult.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo960266h