(+)-(15S)-hydroxyboehmeriasin A | 1219609-57-0

• 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: (+)-(15S)-hydroxyboehmeriasin A
• 英文别名: (14aS,15S)-3,6,7-trimethoxy-11,12,13,14,14a,15-hexahydro-9H-phenanthro[9,10-b]quinolizin-15-ol
• CAS: 1219609-57-0
• 化学式: C₂₄H₂₇NO₄
• 分子量: 393.483
• InChiKey: CMONGIHNDXAKGU-GBXCKJPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 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：
  51.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-(15S)-hydroxyboehmeriasin A 在 三乙基硅烷 作用下， 以 三氟乙酸 为溶剂， 反应 10.0h， 生成 (+)-boehmeriasin A 、 (-)-boehmeriasin A
  参考文献：
  名称：

  Highly efficient synthesis of phenanthroquinolizidine alkaloids via Parham-type cycliacylation

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2009.12.135
• 作为产物：
  描述：

  (S)-1-[(9-bromo-2,3,6-trimethoxyphenanthren-10-yl)methyl]-N,N-diethylpiperidine-2-carboxamide 在 正丁基锂 、 四甲基乙二胺 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 正己烷 、 甲醇 为溶剂， 反应 13.0h， 以92%的产率得到(+)-(15S)-hydroxyboehmeriasin A
  参考文献：
  名称：

  Highly efficient synthesis of phenanthroquinolizidine alkaloids via Parham-type cycliacylation

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2009.12.135

文献信息

• Synthesis of new derivatives of boehmeriasin A and their biological evaluation in liver cancer
  作者：Ece Akhan Güzelcan、Ian R. Baxendale、Rengul Cetin-Atalay、Marcus Baumann

  DOI：10.1016/j.ejmech.2019.01.056

  日期：2019.3

  synthesized in short and high yielding processes providing derivatives differing either in the alkaloid's pentacyclic scaffold or its peripheral substitution pattern. These series have enabled, for the first time, comparative studies into key biological properties revealing a new lead compound with exceptionally high activity against liver cancer cell lines in the picomolar range for both well (Huh7, Hep3B

  已经在短而高产率的方法中合成了两个系列的勃姆球菌素A类似物，提供了生物碱的五环骨架或其外围取代方式不同的衍生物。这些系列首次实现了对关键生物学特性的比较研究，揭示了一种新的先导化合物，对皮摩尔级的肝癌细胞系（Huh7，Hep3B和HepG2）和弱（Mahlavu，FOCUS）都具有异常高的活性和SNU475）分化的细胞。细胞死亡的特征是通过细胞色素C释放，PARP蛋白裂解和SubG1细胞周期停滞而引起的细胞凋亡。随后的测试通过氧化应激与原位形成活性氧（ROS）和改变的磷蛋白水平相关联的细胞凋亡。化合物19降低了Akt蛋白的磷酸化，这在肝癌的肿瘤发生过程中起着至关重要的作用。由于其简单的合成方法和令人着迷的生物学特性，这种新的铅化合物可以解决肝癌治疗中尚未解决的挑战。
• 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.