(-)-(2S,4S)-1-[2-(hydroxymethyl)-1,3-dioxolan-4-yl]-4-N-stearoyl-cytosine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (-)-(2S,4S)-1-[2-(hydroxymethyl)-1,3-dioxolan-4-yl]-4-N-stearoyl-cytosine
• 英文别名: N-[1-[(2S,4S)-2-(hydroxymethyl)-1,3-dioxolan-4-yl]-2-oxopyrimidin-4-yl]octadecanamide
• 化学式: C₂₆H₄₅N₃O₅
• 分子量: 479.66
• InChiKey: XWLYFIJIRUIUOU-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  34
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  硬脂酸酐 、 曲沙他滨 以 甲醇 为溶剂， 反应 6.0h， 以20%的产率得到(-)-(2S,4S)-1-[2-(hydroxymethyl)-1,3-dioxolan-4-yl]-4-N-stearoyl-cytosine
  参考文献：
  名称：

  In Vitro Optimization of Non-Small Cell Lung Cancer Activity with Troxacitabine, l-1,3-Dioxolane-cytidine, Prodrugs

  摘要：

  l-1,3-Dioxolane-cytidine, a potent anticancer agent against leukemia, has limited efficacy against solid tumors, perhaps due to its hydrophilicity. Herein, a library of prodrugs were synthesized to optimize in vitro antitumor activity against non-small cell lung cancer. N-4-Substituted fatty acid amide prodrugs of 10-16 carbon chain length demonstrated significantly improved antitumor activity over l-1,3-dioxolane-cytidine. These in vitro results suggest that the in vivo therapeutic efficacy of l-1,3-dioxolane-cytidine against solid tumors may be improved with prodrug strategies.

  DOI：

  10.1021/jm0612923

文献信息

• In Vitro Optimization of Non-Small Cell Lung Cancer Activity with Troxacitabine, <scp>l</scp>-1,3-Dioxolane-cytidine, Prodrugs
  作者：Marco Radi、Auke D. Adema、Jonathan R. Daft、Jong H. Cho、Eveline K. Hoebe、Lou-Ella M. M. Alexander、Godefridus J. Peters、Chung K. Chu

  DOI：10.1021/jm0612923

  日期：2007.5.1

  l-1,3-Dioxolane-cytidine, a potent anticancer agent against leukemia, has limited efficacy against solid tumors, perhaps due to its hydrophilicity. Herein, a library of prodrugs were synthesized to optimize in vitro antitumor activity against non-small cell lung cancer. N-4-Substituted fatty acid amide prodrugs of 10-16 carbon chain length demonstrated significantly improved antitumor activity over l-1,3-dioxolane-cytidine. These in vitro results suggest that the in vivo therapeutic efficacy of l-1,3-dioxolane-cytidine against solid tumors may be improved with prodrug strategies.