The synthesis and biological activity of novel anthracenone-pyranones and anthracenone-furans
| Autor: | Brian W. Skelton, Kersten Matthias Gericke, Jennette A. Sakoff, Scott G. Stewart, Yuki Egoshi, Jayne Gilbert, Kelly A. Young, James E. Rixson, James R. Abraham, Adam McCluskey |
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| Rok vydání: | 2015 |
| Předmět: |
Annulation
Stereochemistry Cell Survival Clinical Biochemistry Pharmaceutical Science Alkyne Antineoplastic Agents Biochemistry Aldehyde chemistry.chemical_compound Inhibitory Concentration 50 Structure-Activity Relationship Cell Line Tumor Drug Discovery Humans Furans Molecular Biology Cell Proliferation chemistry.chemical_classification Anthracenes Neurons Binding Sites Molecular Structure Cell growth Organic Chemistry Biological activity chemistry Chromones Drug Design Chromone Molecular Medicine Growth inhibition Drug Screening Assays Antitumor Carbonylation Neuroglia Protein Binding |
| Zdroj: | Bioorganicmedicinal chemistry. 23(13) |
| ISSN: | 1464-3391 |
| Popis: | An efficient and divergent methodology for the synthesis of new anthracenone-pyranones and anthracenone-furans is described. Key reactions discussed in these syntheses include an aldehyde promoted annulation with a β-keto-sulfoxide, a domino alkyne insertion/carbonylation/Nu-acylation and a DMEDA promoted Castro–Stephens reaction. We also report the in vitro growth inhibition of these compounds in a range of human cancer cells. The natural product BE-26554A displayed good cell growth activity on BE2-C neuroblastoma and SMA glioblastoma cell lines at 0.17 and 0.16 μM (GI50), respectively. Of note, were a CF3 functionalised anthracenone 4-pyranone (chromone) derivative 22, and an anthracenone-furan derivative 54 which displayed 0.20 μM and 0.38 μM growth inhibition, respectively, in the BE2-C neuroblastoma cell line. |
| Databáze: | OpenAIRE |
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