- Title
- The synthesis and biological activity of novel anthracenone-pyranones and anthracenone-furans
- Creator
- Rixson, James E.; Abraham, James R.; Egoshi, Yuki; Skelton, Brian W.; Young, Kelly; Gilbert, Jayne; Sakoff, Jennette A.; Gericke, Kersten M.; McCluskey, Adam; Stewart, Scott G.
- Relation
- Bioorganic and Medicinal Chemistry Vol. 23, Issue 13, p. 3552-3565
- Publisher Link
- http://dx.doi.org/10.1016/j.bmc.2015.04.032
- Publisher
- Elsevier
- Resource Type
- journal article
- Date
- 2015
- Description
- 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 0.16µM (GI50), respectively. Of note, were a CF3 functionalised anthracenone 4-pyranone (chromone) derivative 22, and an anthracenone-furan derivative 54 which displayed 0.20µM and 0.38µM growth inhibition, respectively, in the BE2-C neuroblastoma cell line.
- Subject
- anthrapyranones; natural products; growth inhibition; human cancer cells; Castro–Stephens reaction
- Identifier
- http://hdl.handle.net/1959.13/1339713
- Identifier
- uon:28318
- Identifier
- ISSN:0968-0896
- Language
- eng
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