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

Autor: Kristin Sattler, Manfred Haber, Ulf Pindur, Houshang Erfanian-Abdoust, M. Dräger
Rok vydání: 1993
Předmět:
Zdroj: Monatshefte f�r Chemie Chemical Monthly. 124:559-576
ISSN: 1434-4475
0026-9247
DOI: 10.1007/bf00819524
Popis: 1-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.
Databáze: OpenAIRE