(+)-boehmeriasin A | 1219808-18-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (+)-boehmeriasin A
• 英文别名: (S)-boehmeriasin A；(14aS)-3,6,7-trimethoxy-11,12,13,14,14a,15-hexahydro-9H-phenanthro[9,10-b]quinolizine
• CAS: 1219808-18-0
• 化学式: C₂₄H₂₇NO₃
• 分子量: 377.483
• InChiKey: ANTGAFQZQJMDNP-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,6,7-trimethoxy-11,12,13,14,14a,15-hexahydro-9H-phenanthro[9,10-b]quinolizin-9-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (+)-boehmeriasin A
  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

• Highly efficient synthesis of phenanthroquinolizidine alkaloids via Parham-type cycliacylation
  作者：Ziwen Wang、Qingmin Wang

  DOI：10.1016/j.tetlet.2009.12.135

  日期：2010.3

  A concise and efficient route involving Parham-type cycliacylation as the key step has been used to synthesize phenanthroquinolizidine alkaloids 1a-c and 2a-c. Among the products, 1b-(S), 1b-(R), 2a-(14S,15S), 2a-(14aR,15R), and 2b were synthesized for the first time. (C) 2010 Elsevier Ltd. All rights reserved.
• 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.