12-N-(4-picolyl)sophoridine butyric acid | 1616292-51-3

• 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: 12-N-(4-picolyl)sophoridine butyric acid
• 英文别名: 4-[(5R,6R,9R,13S)-7-(pyridin-4-ylmethyl)-1,7-diazatricyclo[7.3.1.05,13]tridecan-6-yl]butanoic acid
• CAS: 1616292-51-3
• 化学式: C₂₁H₃₁N₃O₂
• 分子量: 357.496
• InChiKey: XLRQPMYVWOJXLH-XCJLJZCSSA-N

物化性质

• 熔点：
  151-154 °C
• 沸点：
  525.7±45.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  56.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  槐定碱 在 盐酸 、 水 、 三乙胺 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 11.0h， 生成 12-N-(4-picolyl)sophoridine butyric acid
  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

文献信息

• Novel N-substituted sophoridinol derivatives as anticancer agents
  作者：Chong-Wen Bi、Cai-Xia Zhang、Ying-Hong Li、Sheng Tang、Hong-Bin Deng、Wu-Li Zhao、Zhen Wang、Rong-Guang Shao、Dan-Qing Song

  DOI：10.1016/j.ejmech.2014.04.069

  日期：2014.6

  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.