((2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl octadecyl (3-((3-aminopropyl)amino)propyl)phosphoramidate | 943985-20-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: ((2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl octadecyl (3-((3-aminopropyl)amino)propyl)phosphoramidate
• CAS: 943985-20-4
• 化学式: C₃₄H₆₅N₈O₆P
• 分子量: 712.914
• InChiKey: OKKHUWRFUYBMTD-XPDKPEDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.13
• 重原子数：
  49.0
• 可旋转键数：
  31.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  198.46
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  ((2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl octadecyl (3-((3-aminopropyl)amino)propyl)phosphoramidate 、 cholic acid N-succinimidyl ester 以 氯仿 为溶剂， 生成
  参考文献：
  名称：

  Design, synthesis, and antitumor activity of bile acid–polyamine–nucleoside conjugates

  摘要：

  A series of bile acid-polyamine amides conjugated with 3 '-azido-3 '-deoxythymidine (AZT) as potential antitumor prodrugs in the form of phosphoramidates were synthesized in good yields and their antitumor activities were assayed against two human cancer cells in vitro: cervix cancer HeLa cells and renal cancer 7860 cells. The improved antitumor activity probably derived from the enhanced delivery efficiency of AZT due to bile acid-polyamine conjugates. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.067
• 作为产物：
  描述：

  3,3'-二氨基二丙基胺 、 [(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl octadecyl hydrogen phosphate 在 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 0.33h， 以92%的产率得到((2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl octadecyl (3-((3-aminopropyl)amino)propyl)phosphoramidate
  参考文献：
  名称：

  Design, synthesis, and antitumor activity of bile acid–polyamine–nucleoside conjugates

  摘要：

  A series of bile acid-polyamine amides conjugated with 3 '-azido-3 '-deoxythymidine (AZT) as potential antitumor prodrugs in the form of phosphoramidates were synthesized in good yields and their antitumor activities were assayed against two human cancer cells in vitro: cervix cancer HeLa cells and renal cancer 7860 cells. The improved antitumor activity probably derived from the enhanced delivery efficiency of AZT due to bile acid-polyamine conjugates. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.067