(6S,6aS,8S,9S,11S)-9-chloro-5,8-dimethoxy-5,6a,7,8,9,11-hexahydro-6,11-methano[1,3]dioxolo[4',5':4,5]benzo[1,2-e]benzo[b]azepine | 1138334-53-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (6S,6aS,8S,9S,11S)-9-chloro-5,8-dimethoxy-5,6a,7,8,9,11-hexahydro-6,11-methano[1,3]dioxolo[4',5':4,5]benzo[1,2-e]benzo[b]azepine
• CAS: 1138334-53-8
• 化学式: C₁₈H₂₀ClNO₄
• 分子量: 349.814
• InChiKey: HWKDIICHYCZTPM-PJFRXGFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  40.16
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  haemanthidine 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以74%的产率得到(6S,6aS,8S,9S,11S)-9-chloro-5,8-dimethoxy-5,6a,7,8,9,11-hexahydro-6,11-methano[1,3]dioxolo[4',5':4,5]benzo[1,2-e]benzo[b]azepine
  参考文献：
  名称：

  Bioactive Montanine Derivatives from Halide-induced Rearrangements of Haemanthamine-type Alkaloids. Absolute Configuration by VCD

  摘要：

  An unexpected rearrangement of haemanthamine-type alkaloids in the presence of halogenating agents has been found. Rearranged compounds present the 5,11-methanomorphantridine framework characteristic of montanine-type alkaloids. These compounds are difficult to obtain because of their scarcity in natural sources and because the synthetic approaches developed so far require numerous steps. Vibrational circular dichroism (VCD) spectroscopy was used to determine the absolute configuration of one of the rearranged compounds. Several rearranged alkaloids showed antimalarial activity.

  DOI：

  10.1021/ol900065x

文献信息

• Antiproliferative and Structure Activity Relationships of Amaryllidaceae Alkaloids
  作者：Juan Cedrón、Ángel Ravelo、Leticia León、José Padrón、Ana Estévez-Braun

  DOI：10.3390/molecules200813854

  日期：——

  The antiproliferative activity of a set of seven natural Amaryllidaceae alkaloids and 32 derivatives against four cancer cell lines (A2780, SW1573, T47-D and WiDr) was determined. The best antiproliferative activities were achieved with alkaloids derived from pancracine (2), haemanthamine (6) and haemantidine (7). For each skeleton, some structure-activity relationships were outlined.

  确定了一组七种天然金莲花科生物碱和32种衍生物对四种癌细胞系（A2780，SW1573，T47-D和WiDr）的抗增殖活性。源自潘克拉辛（2），血红花胺（6）和雷曼替丁（7）的生物碱具有最佳的抗增殖活性。对于每个骨架，概述了一些构效关系。