2-(2-bromo-4,5-dimethoxyphenyl)-1-(2-(2-(4-methoxyphenyl)-2-oxoethyl)piperidin-1-yl)ethanone | 1227366-14-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-bromo-4,5-dimethoxyphenyl)-1-(2-(2-(4-methoxyphenyl)-2-oxoethyl)piperidin-1-yl)ethanone
• 英文别名: 2-(2-bromo-4,5-dimethoxyphenyl)-1-{(2R)-2-[2-(4-methoxyphenyl)-2-oxoethyl]piperidin-1-yl}ethanone；2-[(2R)-1-[2-(2-bromo-4,5-dimethoxyphenyl)acetyl]piperidin-2-yl]-1-(4-methoxyphenyl)ethanone
• CAS: 1227366-14-4
• 化学式: C₂₄H₂₈BrNO₅
• 分子量: 490.394
• InChiKey: RQBWFOVLYXDZAI-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-bromo-4,5-dimethoxyphenyl)-1-(2-(2-(4-methoxyphenyl)-2-oxoethyl)piperidin-1-yl)ethanone 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以69%的产率得到3-(2-bromo-4,5-dimethoxyphenyl)-2-(4-methoxyphenyl)-1,6,7,8,9,9a-hexahydroquinolizin-4-one
  参考文献：
  名称：

  勃姆星菌素 A 的首次不对称合成

  摘要：

  描述了菲喹唑啶生物碱 (R)-勃姆菌素 A 的第一个不对称合成。通过对 (-)-(S)-1-氨基-2-(甲氧基甲基)吡咯烷腙进行高度非对映选择性的 1,2-亲核加成与闭环复分解，以确保哌啶模板的构建。随后的酰化/氧化/羟醛缩合/自由基环化序列完成了标题 (R) 配置的天然产物的组装。

  DOI：

  10.1002/ejoc.200901404
• 作为产物：
  描述：

  1-(4-methoxyphenyl)-2-(1-tert-butoxycarbonylpiperidin-2-yl)ethanone 在 甲醇 、 三甲基氯硅烷 、 N,N-二异丙基乙胺 、 O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 2-(2-bromo-4,5-dimethoxyphenyl)-1-(2-(2-(4-methoxyphenyl)-2-oxoethyl)piperidin-1-yl)ethanone
  参考文献：
  名称：

  Boehmeriasin A as new lead compound for the inhibition of topoisomerases and SIRT2

  摘要：

  Two synthetic approaches to boehmeriasin A are described. A gram scale racemic preparation is accompanied by an efficient preparation of both the pure enantiomers using the conformationally stable 2-piperidin-2-yl acetaldehyde as starting material. The anti-proliferative activity in three cancer cell lines (CEM, HeLa and L1210) and two endothelial cell lines (HMEC-1, BAEC) indicates promising activity at the nanomolar range. Topoisomerases and SIRT2 are identified as biological targets and the experimental data has been supported by docking studies. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.01.038

文献信息

• First Asymmetric Synthesis of Boehmeriasin A
  作者：David Dumoulin、Stéphane Lebrun、Axel Couture、Eric Deniau、Pierre Grandclaudon

  DOI：10.1002/ejoc.200901404

  日期：2010.4

  The first asymmetric synthesis of phenanthroquinolizidine alkaloid (R)-boehmeriasin A is described. Two alternative synthetic pathways to the key intermediate (RS,R)-4 were achieved through a combination of highly diastereoselective 1,2-nucleophilic addition on (―)-(S)-1-amino-2-(methoxymethyl)pyrrolidine hydrazones with a ring-closing metathesis to ensure the construction of the piperidine template

  描述了菲喹唑啶生物碱 (R)-勃姆菌素 A 的第一个不对称合成。通过对 (-)-(S)-1-氨基-2-(甲氧基甲基)吡咯烷腙进行高度非对映选择性的 1,2-亲核加成与闭环复分解，以确保哌啶模板的构建。随后的酰化/氧化/羟醛缩合/自由基环化序列完成了标题 (R) 配置的天然产物的组装。
• Boehmeriasin A as new lead compound for the inhibition of topoisomerases and SIRT2
  作者：Michael S. Christodoulou、Francesco Calogero、Marcus Baumann、Aída Nelly García-Argáez、Stefano Pieraccini、Maurizio Sironi、Federico Dapiaggi、Raffaella Bucci、Gianluigi Broggini、Silvia Gazzola、Sandra Liekens、Alessandra Silvani、Maija Lahtela-Kakkonen、Nadine Martinet、Alfons Nonell-Canals、Eduardo Santamaría-Navarro、Ian R. Baxendale、Lisa Dalla Via、Daniele Passarella

  DOI：10.1016/j.ejmech.2015.01.038

  日期：2015.3

  Two synthetic approaches to boehmeriasin A are described. A gram scale racemic preparation is accompanied by an efficient preparation of both the pure enantiomers using the conformationally stable 2-piperidin-2-yl acetaldehyde as starting material. The anti-proliferative activity in three cancer cell lines (CEM, HeLa and L1210) and two endothelial cell lines (HMEC-1, BAEC) indicates promising activity at the nanomolar range. Topoisomerases and SIRT2 are identified as biological targets and the experimental data has been supported by docking studies. (C) 2015 Elsevier Masson SAS. All rights reserved.