2-O-(2-fluorobenzoyl)maslinic acid

• 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: 2-O-(2-fluorobenzoyl)maslinic acid
• 英文别名: (4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-11-(2-fluorobenzoyl)oxy-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• 化学式: C₃₇H₅₁FO₅
• 分子量: 594.807
• InChiKey: PNDPZRWXKGUQTO-VCIHGHCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  43
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  山楂酸 、 邻氟苯甲酰氯 在 吡啶 作用下， 以56%的产率得到2-O-(2-fluorobenzoyl)maslinic acid
  参考文献：
  名称：

  2-O-(2-chlorobenzoyl) maslinic acid triggers apoptosis in A2780 human ovarian carcinoma cells

  摘要：

  Depending on the conditions of the reactions, maslinic acid can be converted into the corresponding 2-O-, 3-O-, or 2,3-di-O-acylated compounds in good yields. These compounds showed in SRB assays a significantly increased cytotoxicity as compared to the parent compound maslinic acid. For the most active compound of this series, i.e. 2-O-(2-chlorobenzoyl) maslinic acid (5), more detailed cell biological tests (i.e. AO/PI dye exclusion experiments, an annexin V assay, and microscopic investigations) on A2780 (human ovarian carcinoma cells) revealed that this compound triggers apoptosis. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.07.049

文献信息

• 2-O-(2-chlorobenzoyl) maslinic acid triggers apoptosis in A2780 human ovarian carcinoma cells
  作者：Immo Serbian、Bianka Siewert、Ahmed Al-Harrasi、René Csuk

  DOI：10.1016/j.ejmech.2019.07.049

  日期：2019.10

  Depending on the conditions of the reactions, maslinic acid can be converted into the corresponding 2-O-, 3-O-, or 2,3-di-O-acylated compounds in good yields. These compounds showed in SRB assays a significantly increased cytotoxicity as compared to the parent compound maslinic acid. For the most active compound of this series, i.e. 2-O-(2-chlorobenzoyl) maslinic acid (5), more detailed cell biological tests (i.e. AO/PI dye exclusion experiments, an annexin V assay, and microscopic investigations) on A2780 (human ovarian carcinoma cells) revealed that this compound triggers apoptosis. (C) 2019 Elsevier Masson SAS. All rights reserved.