Photochemical electrocyclisation of 3-vinylindoles to pyrido[2,3-a]-, pyrido[4,3-a]- and thieno[2,3-a]-carbazoles: Design, synthesis, DNA binding and antitumor cell cytotoxicity
| Autor: | Marie-Hélène David-Cordonnier, Thomas Lemster, Gaëlle Lenglet, Ulf Pindur, Christelle Dassi, Sabine Depauw |
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| Rok vydání: | 2009 |
| Předmět: |
Indoles
Cell Survival Stereochemistry Carbazoles Fluorescence spectrometry Antineoplastic Agents Stereoisomerism Context (language use) Nucleic Acid Denaturation Chemical synthesis Fluorescence Structure-Activity Relationship Cell Line Tumor Drug Discovery Animals Humans Topoisomerase II Inhibitors Transition Temperature Structure–activity relationship Binding site Cell Proliferation Pharmacology Binding Sites biology Chemistry Circular Dichroism Topoisomerase Cell Cycle Organic Chemistry DNA General Medicine Photochemical Processes DNA Minor Groove Binding Cyclization Drug Design biology.protein Cattle Spectrophotometry Ultraviolet Topoisomerase I Inhibitors |
| Zdroj: | European Journal of Medicinal Chemistry. 44:3235-3252 |
| ISSN: | 0223-5234 |
| DOI: | 10.1016/j.ejmech.2009.03.026 |
| Popis: | In the context of the design and synthesis of DNA ligands, some new hetarene annelated carbazoles were synthesized. As lead structure the intercalating tetracyclic systems pyrido[2,3-a]- and pyrido[4,3-a]-carbazoles and in one case a thieno[2,3-a]-carbazole were taken into account. A dialkyl amino amidic chain was introduced to the planar chromophoric system with the intent to generate minor groove binding properties. The cytotoxicity of some compounds was examined by the NCI antitumor screening. Furthermore, biophysical as well as biochemical studies were performed in order to get some information about the DNA-binding properties and inhibition of DNA related functional enzymes of this new series of molecules. |
| Databáze: | OpenAIRE |
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