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
The School of Chemistry and Biochemistry, The University of Western Australia, Crawley, WA 6009, Australia.
The School of Chemistry and Biochemistry, The University of Western Australia, Crawley, WA 6009, Australia; Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan.
Bioorg Med Chem. 2015 Jul 1;23(13):3552-65. doi: 10.1016/j.bmc.2015.04.032. Epub 2015 Apr 22.
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.
本文描述了一种高效且多样的合成新的蒽醌-吡喃酮和蒽醌-呋喃的方法。这些合成中讨论的关键反应包括醛促进的与β-酮亚砜的环化反应、多米诺炔烃插入/羰基化/亲核酰化反应以及DMEDA促进的卡斯特罗-斯蒂芬斯反应。我们还报告了这些化合物在一系列人类癌细胞中的体外生长抑制情况。天然产物BE-26554A在BE2-C神经母细胞瘤和SMA胶质母细胞瘤细胞系中分别以0.17和0.16μM（GI50）显示出良好的细胞生长活性。值得注意的是，一种CF3官能化蒽醌4-吡喃酮（色酮）衍生物22和一种蒽醌-呋喃衍生物54在BE2-C神经母细胞瘤细胞系中分别显示出0.20μM和0.38μM的生长抑制作用。
