2α-methoxy-3β-hydroxyolean-12-en-28-oic acid benzylamide

• 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: 2α-methoxy-3β-hydroxyolean-12-en-28-oic acid benzylamide
• 英文别名: (4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-N-benzyl-10-hydroxy-11-methoxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxamide
• 化学式: C₃₈H₅₇NO₃
• 分子量: 575.875
• InChiKey: HZAXCKMJSMEHHL-FRXNWTSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  42
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  山楂酸 在 甲醇 、 4-二甲氨基吡啶 、 草酰氯 、 sodium hydride 、 三乙胺 、 N,N-二甲基甲酰胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 166.58h， 生成 2α-methoxy-3β-hydroxyolean-12-en-28-oic acid benzylamide 、 2α,3β-dimethoxyolean-12-en-28-oic acid benzylamide
  参考文献：
  名称：

  Urea derivates of ursolic, oleanolic and maslinic acid induce apoptosis and are selective cytotoxic for several human tumor cell lines

  摘要：

  2,3-Di-O-acetyl-maslinic acid benzylamide (5) has previously been shown to possess high cytotoxicity for a variety of human tumor cell lines while being of low cytotoxicity to non-malignant cells. Structural modifications performed on 5 revealed that the presence of these acetyl groups in 5 and the presence of (2 beta,3 beta)-configurated centers seems necessary for obtaining high cytotoxicity combined with best selectivity between malignant cells and non-malignant mouse fibroblasts. Compounds carrying an ursane skeleton showed weaker cytotoxicity than their oleanane derived analogs. In addition, the benzylamide function in compound 5 should be replaced by a phenylurea moiety to gain better cytotoxicity while retaining and improving the selectivity. Thus, maslinic acid derived N-[2 beta,3 beta-di-O-acetyl-17 beta-amino-28-norolean-12-en-17-yliphenylurea (45) gave best results showing EC50 = 0.9 mu M (for A2780 ovarian cancer cells) with EC50 > 120 mu M for fibroblasts (NIH 3T3) and triggered apoptosis while caspase-3 was not activated by this compound. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.04.051

文献信息

• Urea derivates of ursolic, oleanolic and maslinic acid induce apoptosis and are selective cytotoxic for several human tumor cell lines
  作者：Sven Sommerwerk、Lucie Heller、Julia Kuhfs、René Csuk

  DOI：10.1016/j.ejmech.2016.04.051

  日期：2016.8

  2,3-Di-O-acetyl-maslinic acid benzylamide (5) has previously been shown to possess high cytotoxicity for a variety of human tumor cell lines while being of low cytotoxicity to non-malignant cells. Structural modifications performed on 5 revealed that the presence of these acetyl groups in 5 and the presence of (2 beta,3 beta)-configurated centers seems necessary for obtaining high cytotoxicity combined with best selectivity between malignant cells and non-malignant mouse fibroblasts. Compounds carrying an ursane skeleton showed weaker cytotoxicity than their oleanane derived analogs. In addition, the benzylamide function in compound 5 should be replaced by a phenylurea moiety to gain better cytotoxicity while retaining and improving the selectivity. Thus, maslinic acid derived N-[2 beta,3 beta-di-O-acetyl-17 beta-amino-28-norolean-12-en-17-yliphenylurea (45) gave best results showing EC50 = 0.9 mu M (for A2780 ovarian cancer cells) with EC50 > 120 mu M for fibroblasts (NIH 3T3) and triggered apoptosis while caspase-3 was not activated by this compound. (C) 2016 Elsevier Masson SAS. All rights reserved.