N¹,N⁹-bis(3β-acetoxyurs-12-en-28-oyl)-diethylenetriamine | 856419-52-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N¹,N⁹-bis(3β-acetoxyurs-12-en-28-oyl)-diethylenetriamine
• 英文别名: [(3S,4aR,6aR,6bS,8aS,11R,12S,12aS,14aR,14bR)-8a-[2-[2-[[(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-acetyloxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carbonyl]amino]ethylamino]ethylcarbamoyl]-4,4,6a,6b,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picen-3-yl] acetate
• CAS: 856419-52-8
• 化学式: C₆₈H₁₀₉N₃O₆
• 分子量: 1064.63
• InChiKey: CJVFJAFWJXSIEA-JRZQBBDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.7
• 重原子数：
  77
• 可旋转键数：
  12
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N¹,N⁹-bis(3β-acetoxyurs-12-en-28-oyl)-diethylenetriamine 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以95%的产率得到N¹,N⁹-bis(3β-hydroxyurs-12-en-28-oyl)-diethylenetriamine
  参考文献：
  名称：

  The cytotoxic activity of ursolic acid derivatives

  摘要：

  Ursolic acid and 2a-hydroxyursolic acid isolated from apple peels were found to show growth inhibitory activity against four tumor cell lines, HL-60, BGC, Bel-7402 and Hela. Structural modifications were performed on the C-3, C-28 and C-11 positions of ursolic acid and the cytotoxicity of the derivatives was evaluated. The SAR revealed that the triterpenes possessing two hydrogen-bond forming groups (an H-donor and a carbonyl group) at positions 3 and 28 exhibit cytotoxic activity. The configuration at C-3 was found to be important for the activity. Introduction of an amino group increased the cytotoxicity greatly. A 3 beta-amino derivative was 20 times more potent than the parent ursolic acid. The 28-aminoalkyl dimer compounds showed selective cytotoxicity. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.01.001
• 作为产物：
  描述：

  熊果酸乙酸酯 在 草酰氯 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 48.0h， 生成 N¹,N⁹-bis(3β-acetoxyurs-12-en-28-oyl)-diethylenetriamine
  参考文献：
  名称：

  The cytotoxic activity of ursolic acid derivatives

  摘要：

  Ursolic acid and 2a-hydroxyursolic acid isolated from apple peels were found to show growth inhibitory activity against four tumor cell lines, HL-60, BGC, Bel-7402 and Hela. Structural modifications were performed on the C-3, C-28 and C-11 positions of ursolic acid and the cytotoxicity of the derivatives was evaluated. The SAR revealed that the triterpenes possessing two hydrogen-bond forming groups (an H-donor and a carbonyl group) at positions 3 and 28 exhibit cytotoxic activity. The configuration at C-3 was found to be important for the activity. Introduction of an amino group increased the cytotoxicity greatly. A 3 beta-amino derivative was 20 times more potent than the parent ursolic acid. The 28-aminoalkyl dimer compounds showed selective cytotoxicity. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.01.001