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 |
Externí odkaz: |