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The synthesis and biological activity of novel anthracenone-pyranones and anthracenone-furans.

Basic Information

ID: ALA3596100

Journal: Bioorg Med Chem

Title: The synthesis and biological activity of novel anthracenone-pyranones and anthracenone-furans.

Authors: Rixson JE, Abraham JR, Egoshi Y, Skelton BW, Young K, Gilbert J, Sakoff JA, Gericke KM, McCluskey A, Stewart SG.

Abstract: 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.

CiteXplore: 25979375

DOI: 10.1016/j.bmc.2015.04.032

Patent ID:

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