(4-oxa-4-phenyl)butyl (2α,3β)-2,3-dihydroxy-olean-12-en-28-oate | 1532556-47-0

• 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: (4-oxa-4-phenyl)butyl (2α,3β)-2,3-dihydroxy-olean-12-en-28-oate
• 英文别名: (4-oxa-4-phenyl-butyl) 2,3-dihydroxy-olean-12-en-28-oate；3-phenoxypropyl (4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 1532556-47-0
• 化学式: C₃₉H₅₈O₅
• 分子量: 606.887
• InChiKey: IASXBOSZWNOURP-KZLBVNOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.13
• 重原子数：
  44.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  山楂酸 、 3-苯氧基溴丙烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以77%的产率得到(4-oxa-4-phenyl)butyl (2α,3β)-2,3-dihydroxy-olean-12-en-28-oate
  参考文献：
  名称：

  Towards cytotoxic and selective derivatives of maslinic acid

  摘要：

  Several novel esters and amides of maslinic acid were prepared. Their evaluation for cytotoxic activity with a panel of human cancer cell lines using a sulforhodamine B (SRB) assay revealed for some of them a noteworthy activity. The results from annexinV-FITC and caspase-assays as well as from DNA laddering experiments provided evidence for an apoptotic cell death. A diacetylated benzylamide (15) induced a G1/G0 arrest in tumor cells. It also displayed an extraordinary cytotoxicity against human ovarian cancer cells but a 300 times lower toxicity for non-malignant primary human fibroblasts. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.047

文献信息

• Towards cytotoxic and selective derivatives of maslinic acid
  作者：Bianka Siewert、Elke Pianowski、Anja Obernauer、René Csuk

  DOI：10.1016/j.bmc.2013.10.047

  日期：2014.1

  Several novel esters and amides of maslinic acid were prepared. Their evaluation for cytotoxic activity with a panel of human cancer cell lines using a sulforhodamine B (SRB) assay revealed for some of them a noteworthy activity. The results from annexinV-FITC and caspase-assays as well as from DNA laddering experiments provided evidence for an apoptotic cell death. A diacetylated benzylamide (15) induced a G1/G0 arrest in tumor cells. It also displayed an extraordinary cytotoxicity against human ovarian cancer cells but a 300 times lower toxicity for non-malignant primary human fibroblasts. (C) 2013 Elsevier Ltd. All rights reserved.
• Membrane damaging activity of a maslinic acid analog
  作者：Bianka Siewert、René Csuk

  DOI：10.1016/j.ejmech.2013.12.031

  日期：2014.3

  Close inspection of human ovarian cancer cells A2780 in the course of an antitumor screening using maslinic acid analogs revealed for one of the compounds, 4-oxa-4-phenyl-butyl 2,3-dihydroxy-olean-12-en-28-oate (1), an unusual behavior. During the incubation of the cells with 1, at the perimeter of the cells or close by crystals were formed consisting of cholesterol and excess 1. Compound 1 was incorporated into the cell's membrane followed by an extrusion of cholesterol from the lipid rafts. As a consequence of the alterations of the cell membrane, a volume decrease was initiated that triggered apoptosis; this extends previous models on apoptosis initiating mechanisms. (C) 2013 Elsevier Masson SAS. All rights reserved.