TY - JOUR
T1 - The synthesis and biological activity of novel anthracenone-pyranones and anthracenone-furans
AU - Rixson, James
AU - Abraham, J.R.
AU - Egoshi, Y.
AU - Skelton, Brian
AU - Young, K.
AU - Gilbert, J.
AU - Sakoff, J.A.
AU - Gericke, K.M.
AU - Mccluskey, A.
AU - Stewart, Scott
PY - 2015
Y1 - 2015
N2 - © 2015 Elsevier Ltd. 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 0.16 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.
AB - © 2015 Elsevier Ltd. 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 0.16 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.
U2 - 10.1016/j.bmc.2015.04.032
DO - 10.1016/j.bmc.2015.04.032
M3 - Article
C2 - 25979375
SN - 0968-0896
VL - 23
SP - 3552
EP - 3565
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
IS - 13
ER -
