o-chlorobenzyl (2α,3β)-2,3-dihydroxy-olean-12-en-28-oate | 1532556-43-6

• 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: o-chlorobenzyl (2α,3β)-2,3-dihydroxy-olean-12-en-28-oate
• 英文别名: (2-chlorophenyl)methyl (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: 1532556-43-6
• 化学式: C₃₇H₅₃ClO₄
• 分子量: 597.278
• InChiKey: WEAIVUFGPJQAOI-PJVGDJALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.52
• 重原子数：
  42.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  山楂酸 、 2-氯苄溴 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以82%的产率得到o-chlorobenzyl (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