4-[(5R,6R,9R,13S)-7-(2,2-dimethylpropyl)-1,7-diazatricyclo[7.3.1.05,13]tridecan-6-yl]butan-1-ol | 1616292-61-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-[(5R,6R,9R,13S)-7-(2,2-dimethylpropyl)-1,7-diazatricyclo[7.3.1.05,13]tridecan-6-yl]butan-1-ol
• CAS: 1616292-61-5
• 化学式: C₂₀H₃₈N₂O
• 分子量: 322.535
• InChiKey: JVZWIIBAXAULOX-MKXGPGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到4-[(5R,6R,9R,13S)-7-(2,2-dimethylpropyl)-1,7-diazatricyclo[7.3.1.05,13]tridecan-6-yl]butan-1-ol
  参考文献：
  名称：

  Novel N-substituted sophoridinol derivatives as anticancer agents

  摘要：

  Using sophoridine (1) as the lead compound, a series of new N-substituted sophoridinic acid derivatives were designed, synthesized and evaluated for their cytotoxicity. SAR analysis indicated that introduction of a chlorobenzyl on the 12-nitrogen atom of sophoridinol might significantly enhance the anti-proliferative activity. Of the newly synthesized compounds, sophoridinol analogue 9k exhibited a potent effect against six human tumor cell lines (liver, colon, breast, lung, glioma and nasopharyngeal). The mode of action of 9k was to inhibit the DNA topoisomerase I activity, followed by the G0/G1 phase arrest. It also showed a moderate oral bioavailability and good safety in vivo. Therefore, compound 9k has been selected as a novel-scaffold lead for further structural optimizations or as a chemical probe for exploring anticancer pathways of this kinds of compounds. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.069