Houshang Erfanian-Abdoust

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

Summary1-Alkylpyrano[3,4-b]indol-3-ones3 react via a Diels-Alder step with an aryne or N-phenylmaleimide to furnish the new [b]annellated carbazoles4–10 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 dioxocarbazoles14–16. Compounds4–8 and14–16 with a coplanar skeleton are members of a class of potential DNA intercalators, as has been shown for5 and8 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.Zusammenfassung1-Alkylpyrano[3,4-b]indol-3-one3 reagieren über einen Diels-Alder-Schritt mit Arin oder N-Phenylmaleinimid zu [b]annellierten Carbazolen4–10 in einer Einstufenreaktion. In analoger Weise reagiert ein in situ erzeugtes N-Benzoylindol-2,3-chinodimethan13 mit Chinonen zu den Dioxocarbazolen14–16. Die Verbindungen4–8 und14–16 gehören infolge ihrer coplanaren Struktur zur Klasse potentieller DNA-Interkalatoren. Auf der Basis von Röntgenstrukturanalysen von5 und8 wird die interkalative Bindung mit einer Watson-Crick Minihelix durch Molecular Modeling vorhergesagt.

A One-Pot Access to [b]Annellated Carbazoles as Potential DNA Intercalators via Diels-Alder Reactions with 1-Alkylpyrano[3,4-b]indol-3-ones

1-Alkylpyrano [3,4-b] indol-3-ones (3) react via a Diels-Alder process with arynes or N-phenylmaleimide to furnish [b] annellated carbazoles (4-10) in a one-pot procedure. Compounds (4-8) with a coplanar framework belong to the class of potential DNA intercalators