2,3-seco-19β,28-epoxy-18α-olean-2,3-dicarboxylic acid | 2457-24-1

• 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: 2,3-seco-19β,28-epoxy-18α-olean-2,3-dicarboxylic acid
• 英文别名: (18α,19β) 19,28-epoxy-2,3-seco-oleanane-2,3-dioate；(18α,19β) 19,28-epoxy-2,3-seco-oleanan-2,3-dicarboxylic acid；2,3-Seco-19β,28-epoxy-18αH-oleanan-disaeure-(2,3)；2,3-Seco-19β,28-epoxy-18αH-oleanan-2,3-disaeure；2-[(1R,4R,5R,8R,9R,10R,13R,14R,15R)-9-(carboxymethyl)-4,5,9,16,16-pentamethyl-20-oxapentacyclo[13.3.2.01,14.04,13.05,10]icosan-8-yl]-2-methylpropanoic acid
• CAS: 2457-24-1
• 化学式: C₃₀H₄₈O₅
• 分子量: 488.708
• InChiKey: RKMQDZDEIZSOEC-QDRGDOLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  正溴丁烷 、 2,3-seco-19β,28-epoxy-18α-olean-2,3-dicarboxylic acid 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 以60%的产率得到dibutyl (18α,19β)-19,28-epoxy-2,3-seco-oleanan-2,3-dicarboxylate
  参考文献：
  名称：

  Simple structural modifications confer cytotoxicity to allobetulin

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2015.05.015
• 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 为溶剂， 反应 126.0h， 生成 2,3-seco-19β,28-epoxy-18α-olean-2,3-dicarboxylic acid
  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

• Preparation and nitration of allobetulin seco-derivatives
  作者：A. V. Shernyukov、Email: [e-mail]、I. Ya. Mainagashev、D. V. Korchagina、Yu. V. Gatilov、N. F. Salakhutdinov、G. A. Tolstikov

  DOI：10.1007/s10600-012-0392-0

  日期：2012.11

  2-Nitro-derivatives of allobetulone were prepared by reaction of allobetulin with nitric acid. 2β-Aminoallobetulin was synthesized by reduction of 2-nitrobetulone with LiAlH4. The corresponding allobetulin seco-derivatives were obtained via oxidation by H2O2 in the presence of K2CO3 of 2-nitroallobetulone and cleavage of 2,2-dinitroallobetulone by K2CO3 in H2O:THF.

  通过将全贝图醇与硝酸反应，制备了全贝图醇的2-硝基衍生物。通过用LiAlH4还原2-硝基贝图醇合成了2β-氨基全贝图醇。相关的全贝图醇分离衍生物是通过在K2CO3存在下用H2O2氧化2-硝基全贝图醇以及用K2CO3在水：THF中裂解2,2-二硝基全贝图醇获得的。
• 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.
• 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.