New Potential DNA Intercalators of the Carbazole Series from Indole-2,3-quinodimethanes: Synthesis, Crystal Structure, and Molecular Modeling with a Watson-Crick Mini-Helix

Article abstract of DOI:10.1007/BF00819524

1-Alkylpyrano<3,4-b>indol-3-ones 3 react via a Diels-Alder step with an aryne or N-phenylmaleimide to furnish the new annelated carbazoles 4-10 in a one-pot process.In an analogous procedure, the in situ generated N-benzoylindole-2,3-quinodimethane (13) reacted with quinones to furnish the dioxocarbazoles 14-16.Compounds 4-8 and 14-16 with a coplanar skeleton are members of a class of potential DNA intercalators, as has been shown for 5 and 8 by X-ray structural analysis.On the basis of the geometries determined by X-ray crystallography, the intercalative binding of these molecules with a Watson-Crick mini-helix was predicted by molecular modeling methods. Key words: annelated carbazoles; crystal structures; molecular modeling; DNA intercalators.