(18α,19β) diethyl 19,28-epoxy-2,3-seco-oleanane-2,3-dioate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (18α,19β) diethyl 19,28-epoxy-2,3-seco-oleanane-2,3-dioate
• 英文别名: diethyl (18α,19β)-19,28-epoxy-2,3-seco-oleanan-2,3-dicarboxylate；ethyl 2-[(1R,4R,5R,8R,9R,10R,13R,14R,15R)-9-(2-ethoxy-2-oxoethyl)-4,5,9,16,16-pentamethyl-20-oxapentacyclo[13.3.2.01,14.04,13.05,10]icosan-8-yl]-2-methylpropanoate
• 化学式: C₃₄H₅₆O₅
• 分子量: 544.816
• InChiKey: NLTGUYWZLQPDKB-WKKZMNEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  白桦脂醇 在 双氧水 、 硝酸 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 138.0h， 生成 (18α,19β) diethyl 19,28-epoxy-2,3-seco-oleanane-2,3-dioate
  参考文献：
  名称：

  Allobetulin derived seco-oleananedicarboxylates act as inhibitors of acetylcholinesterase

  摘要：

  Ring opening of allobetulone gave either seco-acid 8 or di-acid 4. These acids were converted into esters that were screened by Ellman's assay. A dibutenylester of low cytotoxicity (NIH 3T3 murine embryonic fibroblasts) was shown to be a good mixed-type inhibitor (K-i = 3.39, K-i' = 2.26 mu M) for acetylcholinesterase. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.04.086

文献信息

• Simple structural modifications confer cytotoxicity to allobetulin
  作者：Lucie Heller、Anja Obernauer、René Csuk

  DOI：10.1016/j.bmc.2015.05.015

  日期：2015.7

  A variety of allobetulin derivatives was synthesized from allobetulin or allobetulone. These compounds were screened for their cytotoxic activity using a photometric SRB assay employing six different human tumor cell lines. In summary, opening of ring A of allobetulin in general lowers the cytotoxicity, but the 2,3-seco diethyl ester was highly cytotoxic and remarkable selective for A549 lung carcinoma cells while being significantly less cytotoxic for non-malignant mouse fibroblasts. The introduction of an amino group at position C-3 in the allobetulin skeleton enhances cytotoxicity and furnishes highly cytotoxic compounds. Their selectivity to distinguish between cancer cell and non-malignant cell depends on the configuration at position C-3. (C) 2015 Elsevier Ltd. All rights reserved.
• Allobetulin derived seco-oleananedicarboxylates act as inhibitors of acetylcholinesterase
  作者：Lucie Heller、Stefan Schwarz、Anja Obernauer、René Csuk

  DOI：10.1016/j.bmcl.2015.04.086

  日期：2015.7

  Ring opening of allobetulone gave either seco-acid 8 or di-acid 4. These acids were converted into esters that were screened by Ellman's assay. A dibutenylester of low cytotoxicity (NIH 3T3 murine embryonic fibroblasts) was shown to be a good mixed-type inhibitor (K-i = 3.39, K-i' = 2.26 mu M) for acetylcholinesterase. (C) 2015 Elsevier Ltd. All rights reserved.